Reaction #6346

Reaction equation

KBr

9-benzyloxy-6-chloropurine

ammonia

→

9-Benzyloxyadenine

Solvents

ethanol

Conditions

Workup

1. 1
   TemperatureAfter cooling the suspension
2. 2
   Otherwas evaporated to dryness
3. 3
   Otherthe residue partitioned between chloroform (750 ml) and water (500 ml)
4. 4
   WashThe separated aqueous phase was washed with chloroform (200 ml)
5. 5
   WashThe combined organic phases were washed with water
6. 6
   Dryingdried (MgSO4)
7. 7
   Otherevaporated
8. 8
   Otheraffording an orange solid homogeneous on t.l.c

Procedure

A solution of 9-benzyloxy-6-chloropurine (38.4 g; 0.147 mmol) in ethanol (300 ml) saturated with ammonia was heated at 100° C. in an autoclave for 16 hours. After cooling the suspension was evaporated to dryness and the residue partitioned between chloroform (750 ml) and water (500 ml). The separated aqueous phase was washed with chloroform (200 ml). The combined organic phases were washed with water, dried (MgSO4) and evaporated, affording an orange solid homogeneous on t.l.c. (31.1 g, 87%). IR: νmax (KBr) 3372, 3300, 3187, 3038, 1660, 1637, 1600, 1581 cm-1 ; 1H NMR: δH [(CD3)2SO] 5.3(2H, s, CH2Ar), 6.8(2H, br.s, D2O exchangeable, NH2), 7.3(6H, s, H-8, Ar), 7.7(1H, s, H-2). Found: C, 59.39; H, 4.60; N, 29.07%; m/e 241 0949. C12H11N5O requires: C, 59.73; H, 4.60; N, 29.03%; m/z 241.0964.

Source