Efficient microwave-assisted synthesis of highly functionalized pyrimidine derivatives

被引：44

作者：

Hartung, Christian G. ^{[1
]}

Backes, Alexander C. ^{[1
]}

Felber, Beatrice ^{[1
]}

Missio, Andrea ^{[1
]}

Philipp, Alexander ^{[1
]}

机构：

[1] GPC Biotech AG, D-82152 Martinsried, Germany

来源：

TETRAHEDRON | 2006年 / 62卷 / 43期

关键词：

D O I：

10.1016/j.tet.2006.08.065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A generally applicable one-pot procedure for the rapid, easy, and diverse asymmetric functionalization of pyrimidines was developed that requires minimum efforts for the purification of the final products. 4-Amino-6-aryl-substituted pyrimidines are prepared in good yields by combined microwave-assisted amination and Suzuki-Miyaura cross-coupling reactions. The acid-mediated animation reaction affords the products as easily separable salts in 30-40 min reaction time. (c) 2006 Elsevier Ltd. All rights reserved.

引用

收藏

页码：10055 / 10064

页数：10

相关论文

共 54 条

[1] Suitably functionalised pyrimidines as potential antimycotic agents [J].

Agarwal, N ;

Raghuwanshi, SK ;

Upadhyay, DN ;

Shukla, PK ;

Ram, VJ .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (08) :703-706

[2] Copper(I)-catalyzed synthesis of ferrocenyl aryl ethers [J].

an der Heiden, MR ;

Frey, GD ;

Plenio, H .

ORGANOMETALLICS, 2004, 23 (14) :3548-3551

[3] ANTIFILARIAL DRUGS .3. SYNTHESIS AND ANTIFILARIAL ACTIVITY OF N-[4-[[4-ALKOXY-3-[(DIALKYLAMINO)METHYL]PHENYL]AMINO]-2-PYRIMIDINYL]-N'-PHENYLGUANIDINES [J].

ANGELO, M ;

ORTWINE, D ;

WORTH, D ;

WERBEL, LM ;

MCCALL, JW .

JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (09) :1258-1267

[4] Cyclin-dependent kinase 4 inhibitors as a treatment for cancer. Part 1: Identification and optimisation of substituted 4,6-bis anilino pyrimidines [J].

Beattie, JF ;

Breault, GA ;

Ellston, RPA ;

Green, S ;

Jewsbury, PJ ;

Midgley, CJ ;

Naven, RT ;

Minshull, CA ;

Pauptit, RA ;

Tucker, JA ;

Pease, JE .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (18) :2955-2960

[5] A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds [J].

Billingsley, Kelvin L. ;

Anderson, Kevin W. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (21) :3484-3488

[6] Improved yields of meta-amination and symmetrical and unsymmetrical diamination of benzenes [J].

Brown, GR ;

Foubister, AJ ;

Roberts, CA ;

Wells, SL ;

Wood, R .

TETRAHEDRON LETTERS, 2001, 42 (23) :3917-3919

[7] Ullmann diaryl ether synthesis: Rate acceleration by 2,2,6,6-tetramethylheptane-3,5-dione [J].

Buck, E ;

Song, ZJ ;

Tschaen, D ;

Dormer, PG ;

Volante, RP ;

Reider, PJ .

ORGANIC LETTERS, 2002, 4 (09) :1623-1626

[8] Expedient parallel synthesis of 2-amino-4-heteroarylpyrimidines [J].

Bursavich, MG ;

Lombardi, S ;

Gilbert, AM .

ORGANIC LETTERS, 2005, 7 (19) :4113-4116

[9] Efficient Pd-catalyzed amination of heteroaryl halides [J].

Charles, MD ;

Schultz, P ;

Buchwald, SL .

ORGANIC LETTERS, 2005, 7 (18) :3965-3968

[10] Pd-catalyzed coupling reaction of glycosylamines with 6-chloropurines:: Synthesis of 6-(β-D-mannopyranosylamino)-9H-purine and its β-D-gluco isomer, N-glycoside models for spicamycin and septacidin [J].

Chida, N ;

Suzuki, T ;

Tanaka, S ;

Yamada, I .

TETRAHEDRON LETTERS, 1999, 40 (13) :2573-2576

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