Tetrahydrofuran → HCID 69584260, compound

Participants

Reaction Steps

(S)-7-(4-Fluoro-phenylamino)-1-(2-tert-butyl-diphenyl-silanyloxy-1-methyl-ethyl)-3-(4-methoxy-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (0.30 g, 0.45 mmol) was dissolved in anhydrous tetrahydrofuran (3.5 mL) and treated with tetrabutylammonium fluoride (1.0 M in tetrahydrofuran, 1.80 mL, 1.80 mmol) (Aldrich) at room temperature for 6 hours. The reaction was then concentrated. The residue was redissolved in ethyl acetate and washed with water and brine. The organic phase was dried over anhydrous sodium sulfate and concentrated. Purification by flash chromatography (Biotage 40S, ethyl acetate-hexanes gradient [60–100% ethyl acetate]) followed by crystallization from ethyl acetate-hexanes gave (S)-(+)-1-(2-hydroxy-1-methyl-ethyl)-3-(2-fluoro-4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one. (Yield 0.13 g, 66.2%). Melting Point: 188–198° C.

Provenance & Evidence