Patent ID: 6136971
Filing Date: 2000-10-24
Classification: C07D,Y02P

Abstract:
A process for preparing a 1,2-diheteroethylene sulfonamide of the formula: ##STR16## comprising: (a) contacting a pyrimidine monohalide of the formula: ##STR17## with a mono-protected 1,2-diheteroethylene anion of the formula M.sub.1 XCH.sub.2 CH.sub.2 YR.sub.5 in an aprotic nonpolar solvent to produce a mono-protected 1,2-diheteroethylene sulfonamide of the formula: ##STR18## (b) removing R.sub.5 group to produce said 1,2-diheteroethylene sulfonamide,whereinR.sub.1 is hydrogen, lower alkyl, lower alkoxy, lower alkylthio, halogen or trifluoromethyl;R.sub.2 is hydrogen, halogen, lower alkoxy, trifluoromethyl or OCH.sub.2 COOR.sub.a ; andR.sub.3 is hydrogen, halogen, lower alkyl, lower alkylthio, trifluoromethyl, cycloalkyl, lower alkoxy or trifluoromethoxy; orR.sub.2 and R.sub.3 together can be butadienyl, methylenedioxy, ethylenedioxy or isopropylidenedioxy;R.sub.4 is hydrogen, lower alkyl, cycloalkyl, trifluoromethyl, lower alkoxy, lower alkylthio, lower alkylthio-lower alkyl, hydroxy-lower alkyl, hydroxy-lower alkoxy, lower alkoxy-lower alkyl, hydroxy-lower alkoxy-lower alkyl, hydroxy-lower alkoxy-lower alkoxy, lower alkylsulfinyl, lower alkylsulfonyl, 2-methoxy-3-hydroxypropoxy, 2-hydroxy-3-phenylpropyl, amino-lower alkyl, lower alkylamino-lower alkyl, di-lower alkylamino-lower alkyl, amino, lower alkyl-amino, di-lower alkylamino, arylamino, aryl, arylthio, aryloxy, aryl-lower alkyl or heterocyclyl;R.sub.5 is a protecting group;R.sub.6, R.sub.7, R.sub.8 and R.sub.9 are independently hydrogen, halogen, lower alkyl, trifluoromethyl, lower alkoxy, lower alkylthio, hydroxy, hydroxymethyl, cyano, carboxyl, formyl, methylsulfinyl, methylsulfonyl, methylsulfonyloxy or lower alkyloxy-carbonyloxy; orR.sub.7 together with R.sub.6 or R.sub.8 can be butadienyl, methylenedioxy, ethylenedioxy or isopropylidenedioxy;Z is O, S, ethylene, vinylene, C(.dbd.O), OCHR,.sub.10, or SCHR.sub.10 ;R.sub.10 is hydrogen or lower alkyl;X and Y are independently O, S or NH;M is hydrogen, an alkaline metal or an alkaline earth metal;M.sub.1 is an alkaline metal or an alkaline earth metal; andW is halide.