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

HRID 467226Notes

Reaction equation

HRID 467226 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]=2[Cl:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>[O-]CC.[Na+].C(O)C>[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:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:14]([Cl:18])[N:13]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 145239619-Benzyloxy-6-chloro-2-formamidopurine

Product 1

HCID 198136302-Amino-9-benzyloxy-6-chloropurineYield 73.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 2723922Sodium ethoxideSolvent

Procedure

A solution of 9-benzyloxy-6-chloro-2-formamidopurine (3.0g; 9.88mmol) in 0.05M sodium ethoxide in ethanol was heated at reflux temperature for 11/2h and then cooled. Acetic acid (0.5ml) was then added and the solvent removed under vacuo. The residue was purified by column chromatography eluting with chloroform: methanol (50:1) to afford the title compound (2.0g; 73%). υmax (KBr) 3397, 3312, 3205, 1634, 1558, 1505, and 1468cm-1 ; δH [(CD3)2SO] 5.45 (2H, s, CH2Ar), 7.20 (2H, br.s, D2O exchangeable, NH2), 7.50 (5H, s, Ph), 8.15 (1H, s, H-8). (Found: C, 52.74; H, 3.70; N, 25.62%, C12H10N5OCl requires: C, 52.27; H, 3.66; N, 25.41%).

Workup

  1. temperaturecooled
  2. customthe solvent removed under vacuo
  3. customThe residue was purified by column chromatography
  4. washeluting with chloroform: methanol (50:1)

Sources & evidence

ORD record
ord-b91764b331eb47dfb6239d5e1bf535b1
Source dataset
uspto-grants-1992_10
Patent number
US05159076

Reaction notes

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