Acetic Acid → 2-Amino-9-benzyloxy-6-methoxypurine

HRID 373893Notes

Reaction equation

HRID 373893 reaction equation
[CH2:1]([O:8][N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][C:12]([NH:19]C=O)=[N:13][C:14]=2Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].[C:25](O)(=[O:27])C>CO>[NH2:19][C:12]1[N:11]=[C:10]2[C:15]([N:16]=[CH:17][N:9]2[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:14]([O:27][CH3:25])[N:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 145239619-Benzyloxy-6-chloro-2-formamidopurine

Product 1

HCID 145239622-Amino-9-benzyloxy-6-methoxypurineYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 9-benzyloxy-6-chloro-2-formamidopurine (440 mg, 1.60 mmol), 1.2M sodium methoxide in methanol (5.3 ml) and methanol (10 ml) was heated at reflux temperature for 1 hour and then cooled. Acetic acid (4 ml) was added and the solution evaporated to dryness. The residue was suspended in water and extracted with chloroform (2×25 ml). The combined chloroform extracts were washed with brine, dried (magnesium sulphate) and evaporated under reduced pressure. Column chromatography on silica gel (eluted with chloroform-methanol, 100:1) afforded the title compound (331 mg, 76%). IR: υmax (KBr) 3480, 3310, 1625, 1585, 1505, 1485, 1460, 1400 cm-1 ; 1H NMR: δH [(CD3)2SO] 3.96 (3H, s, CH3), 5.31 (2H, s, CH2Ph), 6.64 (2H, br.s, D2O exchangeable, NH2), 7.42 (5H, s, Ph), 7.75 (1H, s, H-8). Found: C, 57.18, H, 4.84; N, 25.85). m/z 271.1075. C13H13N5O2 requires: C, 57.56, H, 4.83, N, 25.82%; m/z 271.1069.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 hour
  3. temperaturecooled
  4. customthe solution evaporated to dryness
  5. extractionextracted with chloroform (2×25 ml)
  6. washThe combined chloroform extracts were washed with brine
  7. dry with materialdried (magnesium sulphate)
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-57e410750202433e988e57b0772accc0
Source dataset
uspto-grants-1992_11
Patent number
US05166198

Reaction notes

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