Helvetica Chimica Acta p. 65 - 72 (1997)
Update date:2022-08-03
Topics:
Obrecht, Daniel
Abrecht, Christine
Grieder, Alfred
Villalgordo, Jose M.
We describe a versatile novel approach for the synthesis of 2,4,6-trisubstituted pyrimidines on solid support. Thus, polymer-bound thiouronium salt 2 reacted in high yield in a cyclocondensation reaction with the acetylenic ketones 3 to form, after tert-butyl-ester cleavage, the polymer-bound carboxylic acids 4, which were cleaved by oxidation with 3-chloroperbenzoic acid and pyrrolidine to form the 2-pyrrolidinylpyrimidine-4-carboxylic acids 6a-c in high yields and purities without further purification (Schemel). Alternatively, acid 4a was subjected to an Ugi four-component condensation which gave the polymer-bound Ugi products 9a-e in good yields (Scheme 2). Multidirectional cleavage reaction of sulfone 8a with different nucleophiles resulted in the clean formation of pyrimidine-4-carboxamides 10-13 (Scheme 3). This strategy combines efficiently solid-phase chemistry with a multicomponent reaction and a multidirectional cleavage step to form highly diverse pyrimidines in a parallel array.
View MoreSynchem Pharma Co.,Ltd(expird)
Contact:+0086-21-61984905-1
Address:Building 60,Zimian Park, LongYang industrial Area, 1515Nong,Yuandong Road Fengxian District, Shanghai ,China
Contact:86-574-26865651
Address:529 YuanBaoShan Road, Beilun District
Fusilin chemical science & technology co., ltd.
Contact:532-80698166/86057573, +86-400-669-7885
Address:School of Material Science & Engineering, Shandong Uinversity of Science & Technology, Huangdao Zone, Qindao, Shandong
Contact:+86-511-88790000
Address:338 North Yushan Rd, Zhenjiang, Jiangsu 212016
Jiacheng-Chem Enterprises Limited(expird)
Contact:86-571-86711508
Address:19 Floor, CIBC Holley International Building, No. 198,Wuxing Road, Hangzhou, China,310020
Doi:10.1016/S0040-4039(97)00233-5
(1997)Doi:10.1016/0040-4020(78)88039-9
(1978)Doi:10.1055/s-1997-764
(1997)Doi:10.1016/S0040-4039(97)00241-4
(1997)Doi:10.1039/b803114b
(2008)Doi:10.1002/anie.202109356
(2021)