Download (4Mb) - Etheses - Saurashtra University

Part-IIExperimentalIR (KBr) cm -1 : 2925(γ C-H ), 1660(γ CONH ), 755(γ C-Cl )8. Synthesis of 2-chloromethyl-5-(4-methoxyphenyl)thieno[2,3-d]pyrimidin-4(3H)-one (Vviii)A mixture of ethyl 2-amino-4-(4-methoxyphenyl)thiophene-3-carboxylate (Ivi, 5.5 gm;0.02 mole), chloroacetonitrile (1.65 gm; 0.022 mole) and catalytic amount of HCl (0.5ml) were reacted under microwave irradiation (25 min) as per procedure described for thecompound Vi. The crude product on recrystallization from methanol-chloroform mixtureyielded 2-chloromethyl-5-(4-methoxyphenyl)thieno[2,3-d]pyrimidin-4(3H)-one (Vviii).M.P. : 205-207 o C (208-210 o C) 2 ; Yield: 84%Mol. Formula : C 14 H 11 ClN 2 O 2 S; Mol. Wt. 306.77IR (KBr) cm -1 : 2990(γ C-H ), 1680(γ C=O ), 746(γ C-Cl )1 H NMR (CDCl 3 )δppm : 3.85 (3H, s, OCH 3 ), 4.48 (2H, s, CH 2 Cl), 6.94-7.54 (5H, m, 4H,Ar-H and 1H at 6), 12.02 (1H, s, NH).9. Synthesis of 2-chloromethyl-5-(4-chlorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one(Vix)A mixture of ethyl 2-amino-4-(4-chlorophenyl)thiophene-3-carboxylate (Iix, 5.6 gm; 0.02mole), chloroacetonitrile (1.65 gm; 0.022 mole) and catalytic amount of HCl (0.5 ml)were reacted under microwave irradiation (20 min) as per procedure described for thecompound Vi. The crude product on recrystallization from methanol-chloroform mixtureyielded 2-chloromethyl-5-(4-chlorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one (Vix).M.P. : 233-234 o C (229-231 o C) 5 ; Yield: 71%Mol. Formula : C 13 H 8 Cl 2 N 2 OS; Mol. Wt. 311.19IR (KBr) cm -1 : 3107(γ NH ), 1649(γ CONH ), 756(γ C-Cl )1 H NMR (CDCl 3 )δppm : 4.54 (2H, s, CH 2 Cl), 7.23-7.57 (5H, m, 4H, Ar-H and 1H at 6),11.5 (1H, s, NH).366