Publication

Novel Solid-phase and Solution-phase Synthetic Methods for Trisubstituted Thieno[3,2-d]pyrimidine Derivatives

조회수 : 154 등록일 : 2016.11.09 00:00

저자 : Lee, DH (Lee, Duck-Hyung)
출처 : BULLETIN OF THE KOREAN CHEMICAL SOCIETY
출판일 : 2016.09.01
 
Novel Solid-phase and Solution-phase Synthetic Methods for Trisubstituted Thieno[3,2-d]pyrimidine Derivatives
 
 
Jeon, MK (Jeon, Moon-Kook)[ 1 ] ; Kim, JG (Kim, Jung-Gyu)[ 1,2 ] ; Lee, DH (Lee, Duck-Hyung)[ 2 ]
 
 
[ 1 ] Korea Res Inst Chem Technol, Bio & Drug Discovery Div, 141 Gajeong Ro, Daejeon 305600, South Korea
[ 2 ] Sogang Univ, Dept Chem, 1 Sogangdae Gil, Seoul 121742, South Korea

 
 
The coupling of 7-aryl-3,4-dihydro-4-oxothieno[3,2-d]pyrimidine-2-carboxylic acid with a primary alkylamine-loaded acid-sensitive methoxy benzaldehyde (AMEBA) resin, a benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP)-mediated amination reaction, and cleavage from the solid support yielded N-alkyl-4-(alkylamino)-7-arylthieno[3,2-d]pyrimidine-2-carboxamide derivatives. The progress of the reactions on solid phase was monitored through attenuated total reflectance-FTIR spectroscopy and was compared with representative solution-phase surrogates. Additionally, N-acylation (acid chloride, InF3 , CH3CN, room temperature) and cyclization (DBN, 1,4-dioxane, 80 degrees C) of a 3-amino-4-(4-t-butoxycarbonylphenyl)thiophene-2-carboxamide intermediate under previously unreported conditions provided 2-substituted thieno[3,2-d]pyrimidin-4(3H)-one derivatives, which were subsequently converted to 2-substituted 4-alkylamino-7-[4-(alkylaminocarbonyl)phenyl]thieno[3,2-d]pyrimidine derivatives through a reaction sequence consisting of a BOP-mediated amination reaction, t-butyl deprotection, and amide formation.
 
 
 
 
 
 
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