Microwave-Assisted Regioselective Suzuki Coupling of 2,4-Dichloropyrimidines with Aryl and Heteroaryl Boronic Acids

被引:4
作者
Dolsak, Ana [1 ]
Mrgole, Kristjan [1 ]
Sova, Matej [1 ]
机构
[1] Univ Ljubljana, Fac Pharm, Askerceva 7, Ljubljana 1000, Slovenia
关键词
cross-coupling; Suzuki; palladium; pyrimidines; synthesis; microwave-assisted;
D O I
10.3390/catal11040439
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Suzuki coupling reaction has been often used for the preparation of a diverse set of substituted pyrimidines. In this study, the Suzuki coupling of 2,4-dichloropyrimidines with aryl and heteroaryl boronic acids was investigated. A thorough screening of reaction conditions and the use of microwave irradiation led to a very efficient and straightforward synthetic procedure providing C4-substituted pyrimidines in good to excellent yields. Short reaction time (15 min) and extremely low catalyst loading (0.5 mol%) are the main advantages of our tetrakis(triphenylphosphine)palladium(0) catalyzed microwave-assisted procedure, which could be used for quick and low-cost regioselective preparation of substituted pyrimidine rings.
引用
收藏
页数:16
相关论文
共 52 条
[41]  
Sica Domenic A, 2004, J Clin Hypertens (Greenwich), V6, P283, DOI 10.1111/j.1524-6175.2004.03585.x
[42]   Synthesis of analogs of the phenylamino-pyrimidine type protein kinase C inhibitor CGP 60474 utilizing a Negishi cross-coupling strategy [J].
Stanetty, P ;
Röhrling, J ;
Schnürch, M ;
Mihovilovic, MD .
TETRAHEDRON, 2006, 62 (10) :2380-2387
[43]   SYNTHESIS OF 2-CHLORO-4,6-DI(HETEROARYL)PYRIMIDINES [J].
STREKOWSKI, L ;
HARDEN, DB ;
GRUBB, WB ;
PATTERSON, SE ;
CZARNY, A ;
MOKROSZ, MJ ;
CEGLA, MT ;
WYDRA, RL .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (05) :1393-1400
[44]  
Sun J., 2018, TOP CHEM MAT ENG, V1, P24, DOI [10.26480/icnmim.01.2018.24.26, DOI 10.26480/ICNMIM.01.2018.24.26]
[45]   The facile route to stereodefined alkenyl-substituted pyrimidines [J].
Tan, JQ ;
Chang, JH ;
Deng, MZ .
SYNTHETIC COMMUNICATIONS, 2004, 34 (20) :3773-3783
[46]   Palladium Nanoparticles Supported on Graphene Oxide as Catalysts for the Synthesis of Diarylketones [J].
Trzeciak, Anna M. ;
Wojcik, Przemyslaw ;
Lisiecki, Radoslaw ;
Gerasymchuk, Yuriy ;
Strek, Wieslaw ;
Legendziewicz, Janina .
CATALYSTS, 2019, 9 (04)
[47]  
VANDERPLAS HC, 1966, RECL TRAV CHIM PAY-B, V85, P1101
[48]  
White CM, 2002, J CLIN PHARMACOL, V42, P963
[49]   Discovery of the Macrocycle 11-(2-Pyrrolidin-1-yl-ethoxy)-14,19-dioxa-5,7,26-triaza-tetracyclo[19.3.1.1(2,6).1(8,12)]heptacosa-1(25),2(26),3,5,8,10,12(27),16,21,23-decaene (SB1518), a Potent Janus Kinase 2/Fms-Like Tyrosine Kinase-3 (JAK2/FLT3) Inhibitor for the Treatment of Myelofibrosis and Lymphoma [J].
William, Anthony D. ;
Lee, Angeline C. -H. ;
Blanchard, Stephanie ;
Poulsen, Anders ;
Teo, Ee Ling ;
Nagaraj, Harish ;
Tan, Evelyn ;
Chen, Dizhong ;
Williams, Meredith ;
Sun, Eric T. ;
Goh, Kee Chuan ;
Ong, Wai Chung ;
Goh, Siok Kun ;
Hart, Stefan ;
Jayaraman, Ramesh ;
Pasha, Mohammed Khalid ;
Ethirajulu, Kantharaj ;
Wood, Jeanette M. ;
Dymock, Brian W. .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (13) :4638-4658
[50]   Rapid "Mix-and-Stir" Preparation of Well-Defined Palladium on Carbon Catalysts for Efficient Practical Use [J].
Yakukhnov, Sergey A. ;
Pentsak, Evgeniy O. ;
Galkin, Konstantin I. ;
Mironenko, Roman M. ;
Drozdov, Vladimir A. ;
Likholobov, Vladimir A. ;
Ananikov, Valentine P. .
CHEMCATCHEM, 2018, 10 (08) :1869-1873