Methanol → 1-(3-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)cyclobutyl)-3-(4-(tert-butyl)phenyl)urea

Participants

Reaction Steps

A solution of N1-(((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)-N1-methylcyclobutane-1,3-diamine (28 mg, 0.072 mmol) and TEA (22 mg, 0.22 mmol) in THF (3 mL) was added dropwise 1-tert-butyl-4-isocyanatobenzene (18 mg, 0.11 mmol) in DCM (0.5 mL). The reaction was stirred for 1 hour at room temperature. The reaction was concentrated and purified by Prep-TLC (twice, DCM:MeOH:NH4OH=300:30:8, V/V) to obtain the desired compound (28 mg, Yield: 88%) as pale white solid. 1H NMR (500 MHz, MeOD): δH 8.29 (s, 1H), 8.24 (s, 1H), 7.28-7.22 (m, 4H), 6.25 (d, J=2.5 Hz, 1H), 5.52-5.50 (m, 1H), 5.07-5.05 (m, 1H), 4.46-4.44 (m, 1H), 3.88-3.85 (m, 1H), 2.97 (brs, 1H), 2.80-2.78 (m, 2H), 2.48-2.42 (m, 2H), 2.30 (s, 3H), 1.84-1.82 (m, 1H), 1.60 (s, 3H), 1.58-1.56 (m, 1H), 1.39 (s, 3H), 1.28 (s, 9H) ppm; ESI-MS (m/z): 565.3 [M+1]+.

Provenance & Evidence