Efficient synthesis of pyrrolo[2,3-d]pyrimidines via a Cu(I)/6-methylpicolinic acid catalyzed coupling reaction

被引:9
作者
Jiang, Xi [1 ]
Sun, Dequn [1 ]
Jiang, Yongwen [2 ]
Ma, Dawei [2 ]
机构
[1] Shangdong Univ Weihai, Marine Coll, Weihai 264209, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
Coupling reaction; Heterocycle; Catalysis; Pyrrolo[2,3-d]pyrimidines; Cyclization; INHIBITORS; ARYL; DERIVATIVES; IODIDES; HALIDES;
D O I
10.1016/j.tetlet.2014.12.098
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper/6-methylpicolinic acid catalyzed coupling reaction of substituted 5-bromopyrimidin-4-amines with alkynes and subsequent cyclization took place in DMSO at 100-110 degrees C to afford 2-chloro-pyrrolo [2,3-d]pyrimidines in moderate to excellent yields. Variable functional groups, including aromatic and aliphatic groups, could be introduced at the 6 and 7 positions using this method. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3259 / 3261
页数:3
相关论文
共 24 条
[1]  
Brazidec J.-Y. L., 2012, BIOORG MED CHEM LETT, V22, P4033
[2]   Pyrrolo[2,3-d]pyrimidines containing an extended 5-substituent as potent and selective inhibitors of lck II [J].
Burchat, AF ;
Calderwood, DJ ;
Hirst, GC ;
Holman, NJ ;
Johnston, DN ;
Munschauer, R ;
Rafferty, P ;
Tometzki, GB .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (19) :2171-2174
[3]   Development of new pyrrolopyrimidine-based inhibitors of Janus kinase 3 (JAK3) [J].
Clark, Michael P. ;
George, Kelly M. ;
Bookland, Roger G. ;
Chen, Jack ;
Laughlin, Steven K. ;
Thakur, Kumar D. ;
Lee, Wenlin ;
Davis, Jan R. ;
Cabrera, Ed J. ;
Brugel, Todd A. ;
VanRens, John C. ;
Laufersweiler, Matthew J. ;
Maier, Jennifer A. ;
Sabat, Mark P. ;
Golebiowski, Adam ;
Easwaran, Vijay ;
Webster, Mark E. ;
De, Biswanath ;
Zhang, George .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (05) :1250-1253
[4]   Mild and efficient copper-catalyzed cyanation of aryl iodides and bromides [J].
Cristau, HJ ;
Ouali, A ;
Spindler, JF ;
Taillefer, M .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (08) :2483-2492
[5]   Synthesis of novel pyrrole and pyrrolo[2,3-d]pyrimidine derivatives bearing sulfonamide moiety for evaluation as anticancer and radiosensitizing agents [J].
Ghorab, Mostafa M. ;
Ragab, Fatma A. ;
Heiba, Helmy I. ;
Youssef, Hanan A. ;
El-Gazzar, Marwa G. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (21) :6316-6320
[6]   BIOACTIVE MARINE METABOLITES .9. MYCALISINE-A AND MYCALISINE-B, NOVEL NUCLEOSIDES WHICH INHIBIT CELL-DIVISION OF FERTILIZED STARFISH EGGS, FROM THE MARINE SPONGE MYCALE SP [J].
KATO, Y ;
FUSETANI, N ;
MATSUNAGA, S ;
HASHIMOTO, K .
TETRAHEDRON LETTERS, 1985, 26 (29) :3483-3486
[7]  
KONDO Y, 1989, CHEM PHARM BULL, V37, P2933
[8]   Assembly of Substituted 3-Methyleneisoindolin-1-ones via a CuI/L-Proline-Catalyzed Domino Reaction Process of 2-Bromobenzamides and Terminal Alkynes [J].
Li, Li ;
Wang, Miao ;
Zhang, Xiaojing ;
Jiang, Yongwen ;
Ma, Dawei .
ORGANIC LETTERS, 2009, 11 (06) :1309-1312
[9]   Assembly of conjugated enynes and substituted indoles via CuI/amino acid-catalyzed coupling of 1-alkynes with vinyl iodides and 2-bromotrifluoroacetanilides [J].
Liu, Feng ;
Ma, Dawei .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (13) :4844-4850
[10]  
LOOMIS CR, 1988, J BIOL CHEM, V263, P1682