Ethanol → 2-Amino-9-hydroxy-6-methoxypurine

HRID 467224Notes

Reaction equation

HRID 467224 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[O:11]CC2C=CC=CC=2)=[C:4]([O:19][CH3:20])[N:3]=1.C(O)C>[Pd].O1CCOCC1>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[OH:11])=[C:4]([O:19][CH3:20])[N:3]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 145239622-Amino-9-benzyloxy-6-methoxypurine

Product 1

HCID 145239632-Amino-9-hydroxy-6-methoxypurine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-amino-9-benzyloxy-6-methoxypurine (300mg, 1.11mmol), 10% palladium-on-charcoal (100mg), ethanol (10ml) and dioxan (5ml) was stirred under an atmosphere of hydrogen for 45 minutes. The catalyst was then removed and the filtrate evaporated to a white solid 2-amino-9-hydroxy-6-methoxypurine (190mg, 95%). IR: υmax (KBr) 3312, 1643, 1591, 1394cm-1 ; 1H NMR: δH [(CD3)2SO] 3.95 (3H, s, CH3), 6.45 (2H, br.s, D2O exchangeable, NH2), 7.93 (1H, s, H-8), 11.75 (1H, br.s, OH). Found: m/e 181.0594. C6H7N5O2 requires: m/e 181.0596.

Workup

  1. customThe catalyst was then removed
  2. customthe filtrate evaporated to a white solid 2-amino-9-hydroxy-6-methoxypurine (190mg, 95%)

Sources & evidence

ORD record
ord-02da322ae3d04aeda52a6c3084db57ff
Source dataset
uspto-grants-1992_10
Patent number
US05159076

Reaction notes

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