An improved synthesis of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine
An improved seven-step synthesis of 4-chloro-7 H -pyrrolo[2,3- d ]pyrimidine from dimethyl malonate with 31% overall yield is described. The procedure is operationally simple and practical for the synthesis of the 4-chloro-7 H -pyrrolo[2,3- d ]pyrimidine building block.
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Published in | Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 54; no. 6; pp. 638 - 642 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
New York
Springer US
01.06.2018
Springer Nature Springer Springer Nature B.V |
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Abstract | An improved seven-step synthesis of 4-chloro-7
H
-pyrrolo[2,3-
d
]pyrimidine from dimethyl malonate with 31% overall yield is described. The procedure is operationally simple and practical for the synthesis of the 4-chloro-7
H
-pyrrolo[2,3-
d
]pyrimidine building block. |
---|---|
AbstractList | An improved seven-step synthesis of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine from dimethyl malonate with 31% overall yield is described. The procedure is operationally simple and practical for the synthesis of the 4-chloro-7H-pyrrolo[2,3-d]pyrimidine building block. An improved seven-step synthesis of 4-chloro-7 H -pyrrolo[2,3- d ]pyrimidine from dimethyl malonate with 31% overall yield is described. The procedure is operationally simple and practical for the synthesis of the 4-chloro-7 H -pyrrolo[2,3- d ]pyrimidine building block. |
Audience | Academic |
Author | Xu, Cheng-Tao Zhang, Yu-Liu Zhu, Yong Luo, Yu Liu, Ting |
Author_xml | – sequence: 1 givenname: Yu-Liu surname: Zhang fullname: Zhang, Yu-Liu organization: Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University – sequence: 2 givenname: Cheng-Tao surname: Xu fullname: Xu, Cheng-Tao organization: Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University – sequence: 3 givenname: Ting surname: Liu fullname: Liu, Ting organization: Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University – sequence: 4 givenname: Yong surname: Zhu fullname: Zhu, Yong organization: Suzhou Highfine Biotech Co., Ltd – sequence: 5 givenname: Yu surname: Luo fullname: Luo, Yu email: yluo@chem.ecnu.edu.cn organization: Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University |
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Cites_doi | 10.1021/jo900157z 10.1136/annrheumdis-2012-202576 10.1111/jvp.12101 10.1358/dof.2014.039.08.2185917 10.2174/1874312901206010232 10.1038/bcj.2013.6 10.1056/NEJMra1202117 10.1039/jr9600000131 10.1016/S0040-4039(00)02219-X 10.1126/science.1071545 10.1021/jo990903e 10.1007/BF00755292 |
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References | Davoll, J. J. Chem. Soc.1960, 131. FurneauxRHTylerPCJ. Org. Chem.199964841110.1021/jo990903e1:CAS:528:DyaK1MXmsFaqsbs%3D11674769 CheungMHarrisPALackeyKETetrahedron Lett.20014299910.1016/S0040-4039(00)02219-X1:CAS:528:DC%2BD3MXhtVahtr8%3D Verstovsek, S.; Mesa. R. A.; Gotlib, J.; Levy, R. S.; Gupta, V.; DiPirso, J. F.; Catalano, J. V.; Deininger, M.; Miller, C.; Silver, R. T.; Talpaz, M.; Winton, E. F.; Harvey, J. H.; Arcasoy, M. O.; Hexner, E.; Lyons, R. M.; Paquette, R.; Raza, A.; Vaddi, K.; Erickson-Viitanen, S.; Koumenis, I. L.; Sun, W.; Sandor, V.; Kantarjian, H. M. N. Engl. J. Med.2012, 366, 799. ZhanLYouDLWuYQXuYNLuoYCN Patent 107011347Chem. Abstr.2017167368362 HaoB-YChenX-ZZhangW-HChin. J. Org. Chem.2010309181:CAS:528:DC%2BC3cXpslSit74%3D Melik-Ogandzhanyan, R. G.; Gapoyan, A. S.; Khachatryan, V. É.; Mirzoyan, V. S. Chem. Heterocycl. Compd.1982, 18, 1305. [Khim. Geterotsikl. Soedin.1982, 1686.] BorosEEThompsonJBKatamreddySRCarpenterAJJ. Org. Chem.200974358710.1021/jo900157z19351107 O'SheaJJKontziasAYamaokaKTanakaYLaurenceAAnn. Rheum. Dis.20137211110.1136/annrheumdis-2012-2025761:CAS:528:DC%2BC3sXntFyntbk%3D Sokolova, V. N.; Magidson, O. Yu. Chem. Heterocycl. Compd.1968, 4, 385. [Khim. Geterotsikl. Soedin.1968, 519.] GonzalesAJBowmanJWFiciGJZhangMMannDWMitton-FryMJ. Vet. Pharmacol. Ther.20143731710.1111/jvp.121011:CAS:528:DC%2BC2cXhtFWjtbnE244951764265276 (a) Laurence, A.; Pesu, M.; Silvennoinen, O.; O'Shea, J. Open Rheumatol. J.2012, 6, 232. (b) O'Shea, J.; Holland, S. M.; Staudt, L. M. N. Engl. J. Med.2013, 368, 161. MaLClaytonJRWalgrenRAZhaoBEvansRJSmithMCHeinz-TahenyKMKreklauELBloemLPitouCShenWStrelowJMHalsteadCRempalaMEParthasarathySGilligJRHeinzLJPeiHWangYStancatoLFDowlessMSIversenPWBurkholderTPBlood Cancer J.2013310910.1038/bcj.2013.6 LiuP-LWangD-JWuY-ZCaoG-FXiaMUS Patent 9714233Chem Abstr.2014161459988 WangAXLiuBNLiuYLiuDKLiuMDrug Eval. Res.2014371691:CAS:528:DC%2BC2cXhvFyru7zK AndrewsMDBagalSKGibsonKROmotoKRyckmansTSkerrattSEStupplePAWO Patent 2012137089Chem. Abstr.2012157606000 AaronsonDSHorvathCMScience2002296165310.1126/science.10715451:CAS:528:DC%2BD38XktlChu7o%3D12040185 TaylorECPatelHHUS Patent 5254687Chem Abstr.1994120164207 Gras, J. Drugs Future2014, 39. 547. Boros, EE (WOS:000265554900056) 2009; 74 Laurence, Arian (MEDLINE:23028408) 2012; 6 DAVOLL, J (WOS:A1960WK69200026) 1960 Verstovsek, S (WOS:000300874300006) 2012; 366 Melik-Ogandzhanyan, R. G. (000441231900012.15) 1982; 18 (000441231900012.2) 1000 Furneaux, RH (WOS:000083520300054) 1999; 64 Wang, A. X. (000441231900012.20) 2014; 37 Cheung, M (WOS:000166894400009) 2001; 42 (000441231900012.1) 1000 (000441231900012.4) 1000 Sokolova, V. N. (000441231900012.18) 1968; 4 Hao, BY (WOS:000279604600021) 2010; 30 Aaronson, DS (WOS:000175976200048) 2002; 296 Gras, J (WOS:000343013900002) 2014; 39 Ma, L (WOS:000318159700002) 2013; 3 Gonzales, AJ (WOS:000339094800001) 2014; 37 O'Shea, JJ (WOS:000313238100006) 2013; 368 O'Shea, JJ (WOS:000316826300016) 2013; 72 (000441231900012.3) 1000 L Ma (2320_CR8) 2013; 3 2320_CR18 2320_CR12 P-L Liu (2320_CR13) 2014; 161 2320_CR15 EE Boros (2320_CR19) 2009; 74 M Cheung (2320_CR11) 2001; 42 AJ Gonzales (2320_CR5) 2014; 37 AX Wang (2320_CR4) 2014; 37 B-Y Hao (2320_CR14) 2010; 30 L Zhan (2320_CR16) 2017; 167 JJ O'Shea (2320_CR6) 2013; 72 MD Andrews (2320_CR17) 2012; 157 DS Aaronson (2320_CR1) 2002; 296 2320_CR7 RH Furneaux (2320_CR10) 1999; 64 EC Taylor (2320_CR9) 1994; 120 cr-split#-2320_CR2.2 cr-split#-2320_CR2.1 cr-split#-2320_CR2.4 cr-split#-2320_CR2.3 2320_CR3 |
References_xml | – volume: 30 start-page: 918 year: 2010 ident: WOS:000279604600021 article-title: Synthesis of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine and 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine publication-title: CHINESE JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Hao, BY – volume: 74 start-page: 3587 year: 2009 ident: WOS:000265554900056 article-title: Facile Reductive Amination of Aldehydes with Electron-Deficient Anilines by Acyloxyborohydrides in TFA: Application to a Diazaindoline Scale-Up publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo900157z contributor: fullname: Boros, EE – volume: 72 start-page: 111 year: 2013 ident: WOS:000316826300016 article-title: Janus kinase inhibitors in autoimmune diseases publication-title: ANNALS OF THE RHEUMATIC DISEASES doi: 10.1136/annrheumdis-2012-202576 contributor: fullname: O'Shea, JJ – volume: 37 start-page: 317 year: 2014 ident: WOS:000339094800001 article-title: Oclacitinib (APOQUEL (R)) is a novel Janus kinase inhibitor with activity against cytokines involved in allergy publication-title: JOURNAL OF VETERINARY PHARMACOLOGY AND THERAPEUTICS doi: 10.1111/jvp.12101 contributor: fullname: Gonzales, AJ – volume: 4 start-page: 385 year: 1968 ident: 000441231900012.18 publication-title: Chem. Heterocycl. Compd. contributor: fullname: Sokolova, V. N. – year: 1000 ident: 000441231900012.1 publication-title: CN Patent – volume: 37 start-page: 169 year: 2014 ident: 000441231900012.20 publication-title: Drug Eval. Res. contributor: fullname: Wang, A. X. – volume: 42 start-page: 999 year: 2001 ident: WOS:000166894400009 article-title: Synthesis of 2-chloro-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one publication-title: TETRAHEDRON LETTERS contributor: fullname: Cheung, M – volume: 296 start-page: 1653 year: 2002 ident: WOS:000175976200048 article-title: A road map for those who don't know JAK-STAT publication-title: SCIENCE contributor: fullname: Aaronson, DS – volume: 39 start-page: 547 year: 2014 ident: WOS:000343013900002 article-title: FILGOTINIB publication-title: DRUGS OF THE FUTURE doi: 10.1358/dof.2014.039.08.2185917 contributor: fullname: Gras, J – volume: 6 start-page: 232 year: 2012 ident: MEDLINE:23028408 article-title: JAK Kinases in Health and Disease: An Update. publication-title: The open rheumatology journal doi: 10.2174/1874312901206010232 contributor: fullname: Laurence, Arian – volume: 18 start-page: 1305 year: 1982 ident: 000441231900012.15 publication-title: Chem. Heterocycl. Compd. contributor: fullname: Melik-Ogandzhanyan, R. G. – volume: 3 start-page: ARTN e109 year: 2013 ident: WOS:000318159700002 article-title: Discovery and characterization of LY2784544, a small-molecule tyrosine kinase inhibitor of JAK2V617F publication-title: BLOOD CANCER JOURNAL doi: 10.1038/bcj.2013.6 contributor: fullname: Ma, L – year: 1000 ident: 000441231900012.3 publication-title: US Patent – year: 1000 ident: 000441231900012.2 publication-title: WO Patent – volume: 64 start-page: 8411 year: 1999 ident: WOS:000083520300054 article-title: Improved syntheses of 3H,5H-pyrrolo[3,2-d]pyrimidines publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Furneaux, RH – start-page: 131 year: 1960 ident: WOS:A1960WK69200026 article-title: PYRROLO[2,3-D]PYRIMIDINES publication-title: JOURNAL OF THE CHEMICAL SOCIETY contributor: fullname: DAVOLL, J – year: 1000 ident: 000441231900012.4 publication-title: US Patent – volume: 366 start-page: 799 year: 2012 ident: WOS:000300874300006 article-title: A Double-Blind, Placebo-Controlled Trial of Ruxolitinib for Myelofibrosis publication-title: NEW ENGLAND JOURNAL OF MEDICINE contributor: fullname: Verstovsek, S – volume: 368 start-page: 161 year: 2013 ident: WOS:000313238100006 article-title: MECHANISMS OF DISEASE JAKs and STATs in Immunity, Immunodeficiency, and Cancer publication-title: NEW ENGLAND JOURNAL OF MEDICINE doi: 10.1056/NEJMra1202117 contributor: fullname: O'Shea, JJ – ident: 2320_CR12 doi: 10.1039/jr9600000131 – volume: 161 start-page: 459988 year: 2014 ident: 2320_CR13 publication-title: Chem Abstr. contributor: fullname: P-L Liu – volume: 74 start-page: 3587 year: 2009 ident: 2320_CR19 publication-title: J. Org. Chem. doi: 10.1021/jo900157z contributor: fullname: EE Boros – ident: 2320_CR3 – volume: 72 start-page: 111 year: 2013 ident: 2320_CR6 publication-title: Ann. Rheum. Dis. doi: 10.1136/annrheumdis-2012-202576 contributor: fullname: JJ O'Shea – volume: 37 start-page: 317 year: 2014 ident: 2320_CR5 publication-title: J. Vet. Pharmacol. Ther. doi: 10.1111/jvp.12101 contributor: fullname: AJ Gonzales – volume: 3 start-page: 109 year: 2013 ident: 2320_CR8 publication-title: Blood Cancer J. doi: 10.1038/bcj.2013.6 contributor: fullname: L Ma – ident: #cr-split#-2320_CR2.2 – ident: #cr-split#-2320_CR2.3 – ident: #cr-split#-2320_CR2.1 – volume: 37 start-page: 169 year: 2014 ident: 2320_CR4 publication-title: Drug Eval. Res. contributor: fullname: AX Wang – volume: 42 start-page: 999 year: 2001 ident: 2320_CR11 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)02219-X contributor: fullname: M Cheung – volume: 157 start-page: 606000 year: 2012 ident: 2320_CR17 publication-title: Chem. Abstr. contributor: fullname: MD Andrews – ident: #cr-split#-2320_CR2.4 – ident: 2320_CR7 doi: 10.1358/dof.2014.039.08.2185917 – volume: 296 start-page: 1653 year: 2002 ident: 2320_CR1 publication-title: Science doi: 10.1126/science.1071545 contributor: fullname: DS Aaronson – volume: 64 start-page: 8411 year: 1999 ident: 2320_CR10 publication-title: J. Org. Chem. doi: 10.1021/jo990903e contributor: fullname: RH Furneaux – volume: 120 start-page: 164207 year: 1994 ident: 2320_CR9 publication-title: Chem Abstr. contributor: fullname: EC Taylor – volume: 167 start-page: 368362 year: 2017 ident: 2320_CR16 publication-title: Chem. Abstr. contributor: fullname: L Zhan – volume: 30 start-page: 918 year: 2010 ident: 2320_CR14 publication-title: Chin. J. Org. Chem. contributor: fullname: B-Y Hao – ident: 2320_CR15 – ident: 2320_CR18 doi: 10.1007/BF00755292 |
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Snippet | An improved seven-step synthesis of 4-chloro-7
H
-pyrrolo[2,3-
d
]pyrimidine from dimethyl malonate with 31% overall yield is described. The procedure is... An improved seven-step synthesis of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine from dimethyl malonate with 31% overall yield is described. The procedure is... |
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SubjectTerms | Chemistry Chemistry and Materials Science Chemistry, Organic Organic Chemistry Pharmacy Physical Sciences Pyrimidines Science & Technology Synthesis |
Title | An improved synthesis of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine |
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