Hydrochloric Acid → 9-Benzyl-2,6-dichloro-9H-purine

Participants

Reaction Steps

A mixture of 9-benzyl-2-chloro-9H-adenine (130 mg., 0.5 mmole) and 1.25 ml. of 1 N sodium n-propoxide in n-propanol in 13 ml. of n-propanol is refluxed overnight, neutralized with hydrochloric acid and evaporated in vacuo. Trituration of residual material with water provides 118 mg. of crude product which crystallized from aqueous ethanol affords 90 mg. (64%) of analytically pure 9-benzyl-2-n-propoxy-9H-adenine, m.p. 178°-180° C. (dec.). IR(KBr): 3280, 3130, 2970, 1660, 1595, 1405, 1350, 1330, 1275 cm-1. UV:λmaxEtOH 254 nm(ε8,800), 269.5 nm(ε12,800). NMR(CDCl3):δ1.02(3H,t,J=7 Hz), 1.6-2.1(2H,m), 4.25(2H,t,J=7 Hz), 5.20(2H,s), 6.00(2H,br.s), 7.23(5H,m), 7.50(1H,s).

Provenance & Evidence