2-Bromopropane → N-Benzyl-2-chloro-9-isopropyl-9H-purin-6-amine

Participants

Reaction Steps

A mixture of 6-benzylamino-2-chloropurine (1) 1.32 g, 5.08 mmol), potassium carbonate (4.3 g, 31 mmol) and isopropylbromide (5.5 ml, 58 mmol) in 35 ml of dry dimethyl sulfoxide was vigorously shaken overnight. The reaction mixture was evaporated in vacuum and then partitioned between water and ethylacetate. The organic layer was dried (sodium sulfate) and evaporated. Crystallization from methanol afforded 1.305 g (85%) of product 2, m.p. 181-182° C. For C15H16N5Cl(301.78) calculated: 59.70% C, 5.34% H, 23.21% N, 11.75% Cl; found: 59.52% C, 5.36% H, 23.01% N. FTIR spectrum (cm−1): 1713, 1626, 1572, 1537, 1497, 1471, 1456, 1425, 1398, 1355, 1314, 1292, 1255, 1228, 1202. ′H NMR (400 MHz, (CH3)2SO): 1.48D (6H, J=6.8, (CH3)2CH); 4.57 m (1H, CH(CH3)2); 4.66bd (2H, J=6.1, CH2); 7.19 ft, (1 H, J=7.2, J=1.7, H-p); 7.27dd (2H, J=7.2, H-m); 7.34dd (2H, J=7.2, J=1.7, H-o); 7.69s (1 H, H-C8).

Provenance & Evidence