Dimethyl Sulfoxide → HCID 69069650, compound

Participants

Reaction Steps

To a stirred solution of (2-fluoro-9-isopropyl-9H-purin-6-yl)-pyridin-2-yl-amine (0.25 g, 0.87 mmol) in BunOH/DMSO (5 mL, 4:1) at RT under Ar was added Pri2NEt (1.5 mL, 8.61 mmol) followed by. (R)-(−)-2-aminobutan-1-ol (0.82 mL, 8.71 mmol). The reaction mixture was placed in a preheated oil bath at 140° C. and stirred at this temperature for 72 h, when TLC (9:1 CHCl3/MeOH) indicated that the reaction had gone to completion. The reaction mixture was allowed to cool to RT and the solvent was evaporated in vacuo. The residue was partitioned between EtOAc (100 mL) and H2O (150 mL), the aqueous, phase was extracted with more EtOAc (2×50 mL), and the combined organic phase was washed with brine (50 mL), dried (MgSO4) and evaporated in vacuo. The residue was purified by gradient column chromatography on silica gel eluted with CHCl3/MeOH (100:0→97:3), to afford the title compound as a white solid (0.29 g, 95%). Mp 30-35° C. 1H-NMR (d6-DMSO, 250 MHz): δ 0.77 (m, 3H, —NHCH(CH2CH3)CH2OH), 1.24-1.48 (m, 8H, —NHCH(CH2CH3)CH2OH+CH(CH3)2), 3.38 (m, 2H, —NHCH(CH2CH3)CH2OH), 3.70 (m, 1H, —NHCH(CH2CH3)CH2OH), 4.52 (m, 2H, —NHCH2-Pyr), 4.75 (m, 2H, OH+CH(CH3)2), 5.81 (d, 2H, J=8.33 Hz, —NHCH(CH2CH3)CH2OH), 7.24, 7.67, 8.48 (3×m, 4H, Pyr), 7.79 (bs, 2H, —N═CH—N+—HNCH2-Pyr). FAB-MS m′z (relative intensity): 356 ([M+H]+, 100), 324 (28), 154 (26), 136 (22). Accurate Mass (M+H: Actual: 356.2199, Measured: 356.2208. Microanalysis (Expected:Measured) C18H25N7O: C, 60.83:61.81; H, 7.09:7.29; N, 27.58:27.09.

Provenance & Evidence