Phosphorus oxychloride → 7-benzyl-2-chloro-1-methyl-1,7-dihydro-6H-purin-6-one

HRID 275334Notes

Reaction equation

HRID 275334 reaction equation
[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:7]=[N:6][C:5]=2[NH:4][C:3]1=O.O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:3]1[N:2]([CH3:1])[C:10](=[O:11])[C:9]2[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:7]=[N:6][C:5]=2[N:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 111186677-benzyl-1-methyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

Product 1

HCID 36530217-benzyl-2-chloro-1-methyl-1,7-dihydro-6H-purin-6-one

Procedure

Heat 1-methyl-7-(phenylmethyl)purine-2,6-dione (8.0 g=31 mmol)in POCl3 (80 ml) at reflux 7 hr. Concentrate in vacuo, partition EtOAc-ice water, wash with water, dry and concentrate. Chromatograph on silica with 98:2 CH2Cl2 /MeOH to obtain the title compound as a foam, FAB MS: M+1=275.

Workup

  1. temperatureat reflux 7 hr
  2. concentrationConcentrate in vacuo
  3. custompartition EtOAc-ice water
  4. washwash with water
  5. customdry
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-1074914a4cf04515a9585617472a151e
Source dataset
uspto-grants-1995_02
Patent number
US05393755

Reaction notes

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