2-Bromopropane → (2-Chloro-9-isopropyl-9H-purin-6-yl)-pyridin-3-ylmethyl-amine

Participants

Reaction Conditions

Reaction Steps

(2-Chloro-9H-purin-6-yl)-pyridin-3-ylmethyl-amine (110.3 g, 0.37 mol) was dissolved in dry DMF (1.5 L) and warmed to 70° C. with stirring. K2CO3 (230 g, 1.67 mol) and 2-bromopropane (300 mL, 3.20 mol) were added and the reaction was stirred at 70° C. overnight. The reaction mixture was allowed to cool to room temperature and K2CO3 was removed by filtration and washing with EtOAc. The combined filtrate and washings were concentrated on a rotary evaporator and then under high vacuum to remove most of the DMF. The resulting residue was stirred vigorously in H2O (1 L) and CH2Cl2 (1 L) until dissolution was complete. The aqueous layer was extracted with more CH2Cl2 (2×200 mL), the organic extracts were combined, dried over MgSO4, and evaporated to afford the title compound (87.2 g, 78%) as a beige powder. 1H-NMR (DMSO-d6): δ1.50-1.53 (6H, d, —CH(CH3)2), 4.67-4.72 (3H, m, —CH2—NH— & —CH(CH3)2), 5.20 (1H, br. s, NH, 7.34-7.39 (dd, ArH), 7.76-7.79 (1H, d, ArH), 8.33 (1H, s, ArH, —N═CH—N—), 8.46-8.48 (1H, d, ArH), 8.61 (1H, s, ArH), 8.92 (1H, br. s, NH.

Provenance & Evidence