Ammonia → 9-(Benzyloxy)-9H-purin-6-amine

HRID 6250Notes

Reaction equation

HRID 6250 reaction equation
[CH2:1]([O:8][N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:19].[K+].[Br-]>C(O)C>[CH2:1]([O:8][N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[NH2:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 253877Potassium BromideHCID 145239689-Benzyloxy-6-chloropurine

Product 1

HCID 123544939-(Benzyloxy)-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. temperatureAfter cooling the suspension
  2. customwas evaporated to dryness
  3. customthe residue partitioned between chloroform (750 ml) and water (500 ml)
  4. washThe separated aqueous phase was washed with chloroform (200 ml)
  5. washThe combined organic phases were washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customaffording an orange solid homogeneous on t.l.c

Sources & evidence

ORD record
ord-b7ee7fbacb394ae7a8be509b810a5cae
Source dataset
uspto-grants-1993_09
Patent number
US05247085

Reaction notes

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