Journal of Sulfur Chemistry 285
3.76–3.89 (q, J = 7.0 Hz, 2H, CH2CH3), 4.30 (s, 2H, COCH2Cl), 7.24 (s, 2H, NH2) 7.34–7.66
(m, 9H, Ar–H) and 13.23 (s, 1H, NH). Anal. for C25H19N3O4SBrCl (572.8): Calcd.: C, 52.42; H,
3.34; N, 7.34; S, 5.60; Br, 13.95; Cl, 6.19. Found: C, 52.63; H, 3.67; N, 7.15; S, 5.34; Br, 13.70;
Cl, 6.32%.
4.29. Ethyl 9-(4-bromophenyl)-2-(chloromethyl)-4-oxo-7-phenyl-3,4-dihydro-
pyrido[3ꢀ,2ꢀ:4,5]thieno[3,2-d]pyrimidine-8-carboxylate (21)
A solution of 20 (10 mmol) in glacial acetic acid (30 ml) containing 5 ml of acetic anhydride
was heated under reflux for 4 h and then cooled. The solid product obtained was filtered off and
crystallized from ethanol to give 21 as yellow crystals (70%), m.p. 278–280◦C. IR υ (cm−1):
1
=
3173 (NH), 1727 (CO-ester), 1652 (C(4) O). H NMR (DMSO-d6): δ 0.78–0.85 (t, J = 7.0 Hz,
3H, CH2CH3), 2.15 (s, 2H, CH2Cl) 3.86–3.97 (q, J = 7.0 Hz, 2H, CH2CH3), 7.346–7.388 (d,
J = 8.4 Hz, 2H, Ar–H), 7.57–7.58 (m, 5H, Ar–H), 7.668–7.710 (d, J = 8.4 Hz, 2H, Ar–H) and
12.85 (s, 1H, NH). Anal. for C25H17N3O3SBrCl (554.8): Calcd.: C, 54.12; H, 3.09; N, 7.57; S,
5.78; Br, 14.40; Cl, 6.39. Found: C, 54.33; H, 3.34; N, 7.32; S, 5.60; Br, 14.62; Cl, 6.66%.
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