o-Fluorobenzaldehyde → 5-[(2-Fluorophenyl)hydroxymethyl]-3-methyl-1-(2-methylpropyl)-6-[[2-(trifluoromethyl)phenyl]methyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Participants

Reaction Steps

5-Bromo-1-isobutyl-3-methyl-6-[2-(trifluoromethyl)benzyl]-thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (Example 1 part c)) (100 mg) was dissolved in tetrahydrofuran (2 mls) and EtMgBr (250 ul of 1M solution in tetrahydrofuran) was added. After 10 mins 2-fluorobenzaldehyde (250 ul of a 1M solution in tetrahydrofuran) was added. After 1 hr the reaction was quenched via addition of water. The reaction was concentrated in vacuo and extracted into dichloromethane, concentrated in vacuo and the residue purified via chromatography eluting with 0-100% diethyl ether in isohexane to yield the title compound (9 mg).

Provenance & Evidence