Dimethyl Disulfide → HCID 10151314, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (−78° C.) solution of 4-[2-(3-chlorophenyl)pyrazolo[1,5-c]pyrimidin-3-yl]-N-cyclopentyl-2-pyrimidinamine (267 mg, 0.683 mmol) in tetrahydrofuran (8 mL) was added lithium diisopropylamide (12.8 mL, 0.16 M in tetrahydrofuran, 2.05 mmol, made from 5 mL n—BuLi (1.6 M in hexanes) and 1.19 mL diisopropylamine in 43.5 mL tetrahydrofuran at 0° C.) dropwise. The reaction mixture was stirred at −78° C. for 10 minutes followed by the addition of methyl disulfide (246 μL, 2.73 mmol). The resultant mixture was stirred at −78° C. for 10 minutes then quenched with water. Upon warming to room temperature, the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (4:1 to 3:1 hexanes:ethyl acetate) provided 4-[2-(3-chlorophenyl)-7-(methylthio)pyrazolo[1,5-c]pyrimidin-3-yl]-N-cyclopentylpyrimidin-2-amine (171 mg, 57%) as a white solid. Rf 0:10 (4:1 hexanes:ethyl acetate); 1H NMR (CDCl3) δ 8.12 (d, 1H), 7.99–7.91 (m, 2H), 7.73 (s,1H), 7.51 (d, 1H), 7.48–7.34 (m, 2H), 6.35 (d,1H), 5.19 (d, 1H), 4.30 (m, 1H), 2.76 (s, 3H), 2.05 (m, 2H), 1.82–1.50 (m, 6H); MS m/z 437 (M+1).

Provenance & Evidence