2-Bromopropane → (2-Fluoro-9-isopropyl-9H-purin-6-yl)-pyridin-4-yl-amine

Participants

Reaction Steps

To a stirred solution of (2-fluoro-9H-purin-6-yl)-pyridin-4-ylmethyl-amine (0.6 g, 2.46 mmol) in DMA (10 mL) under Ar, at RT, was added K2CO3 (powdered, anhydrous, 1.65 g, 11.93 mmol) followed by 2-bromopropane (2.25 mL, 23.96 mmol). The reaction mixture was stirred at RT for 48 h, when TLC (9:1 CHCl3/MeOH) indicated that the reaction had gone to completion. The solvent was evaporated in vacuo and the residue partitioned between H2O (200 mL) and EtOAc (100 mL), the aqueous phase was separated and extracted with more EtOAc (2×50 mL). The bulked organic phase was washed with brine (50 mL), dried (MgSO4) and evaporated in vacuo, and the residue was purified by gradient column chromatography on silica gel, eluted with CHCl3/MeOH (100:0→95:5), to afford the title compound as a white solid (0.40 g, 57%). Mp 270-273° C. 1H-NMR (d6-DMSO, 250 MHz): δ 1.49 (2×s, 6H, —CH(CH3)2), 4.63 (m, 3H, —CH(CH3)2+—HNCH2-Pyr) 7.30, 8.47 (2×m, 4H, Pyr), 8.28 (s, 1H, —N═CH—N—), 8.97 (bs, 1H, —HNCH2-Pyr). FAB-MS m/z (relative intensity): 287 ([M+H)]+, 100), 245 (8), 154 (23), 136 (18). Accurate Mass (M+H): Actual: 287.1420, Measured: 287.1412. Microanalysis (Expected:Measured) C14H15N6F: C, 58.73:58.57; H, 5.28:5.21; N, 29.35:29.27.

Provenance & Evidence