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. 2021 Mar 23;36(1):831–846. doi: 10.1080/14756366.2021.1900158

Scheme 1.

Scheme 1.

Synthesis of 5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4(3H)-one derivatives 7, 14, and 27–57. Reagents and conditions: (a) ethyl 2-cyanoacetate, Sulphur, Et3N, EtOH, reflux, 4 h, 96–100%, (b) 1,1'-thiocarbonylbis(pyridin-2(1H)-one), THF, reflux, 4 h, 80–86%, (c) substituted aniline, EtOH, reflux, 12 h, 84–93%, (d) (i) 10% NaOH/MeOH (1:3), reflux 3 h, (ii) 2 N HCl, 93–98%, (e) 2-bromo-N-substitued acetamide 26, Et3N, MeCN, reflux, 5 h, 33–98%.