Triethylamine → Ethyl 1,2,3,4-tetrahydro-3-methyl-1-(2-methylpropyl)-2,4-dioxo-6-(4-quinolinylmethyl)thieno[2,3-d]pyrimidine-5-carboxylate

Participants

Reaction Steps

Trifluoroacetic anhydride (3.33 ml) was added to a solution of the product of step d) (7.34 g) and triethylamine (6.56 ml) in anhydrous THF (150 ml) at room temperature under nitrogen and the mixture stirred for 15 min. 10% palladium on charcoal (500 mg) was added and the mixture hydrogenated at 1 bar for 20 h. It was filtered through celite washing with saturated sodium bicarbonate solution (150 ml) then ethyl acetate (300 ml). The organic material was extracted into ethyl acetate (150 ml), the combined extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography, eluting with 1:1 ethyl acetate/i-hexane, to give the sub-title compound as a solid (5.90 g). MS(ESI) 452 [M+H]+. δ 1HCDCl3 0.90 (6H,d), 1.37 (3H,t), 2.10-2.16 (1H,m), 3.39 (3H,s), 3.64 (2H,d), 4.45 (2H,q), 4.61 (2H,s), 7.29 (1H,d), 7.60 (1H,t), 7.75 (1H,t), 8.11 (1H,d), 8.16 (1H,d), 8.89 (1H,d)

Provenance & Evidence