Phosphorus oxychloride → 7-Allyl-6-chloro-3-pentyl-3,7-dihydro-2H-purin-2-one

HRID 249770Notes

Reaction equation

HRID 249770 reaction equation
[CH2:1]([N:4]1[C:12]2[C:11](=O)[NH:10][C:9](=[O:14])[N:8]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:7]=2[N:6]=[CH:5]1)[CH:2]=[CH2:3].P(Cl)(Cl)([Cl:22])=O>>[CH2:1]([N:4]1[C:12]2[C:11]([Cl:22])=[N:10][C:9](=[O:14])[N:8]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:7]=2[N:6]=[CH:5]1)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 598538107-Allyl-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 598538197-Allyl-6-chloro-3-pentyl-3,7-dihydro-2H-purin-2-oneYield 71.2%

Procedure

A mixture of 7-allyl-3-pentyl-3,7-dihydro-1H-purine-2,6-dione (0.80 g, 3.0 mmol) and phosphoryl chloride (10.0 mL, 100 mmol) was refluxed for 2 h. The excess phosphoryl chloride was removed by vacuum distillation. The residue was diluted with ice-water, neutralized with solid K2CO3, and then extracted with DCM three times. The combined organic layers were dried, filtered and concentrated to provide the crude product (0.60 g), which was used for next step without further purification. LCMS calculated for C13H18ClN4O (M+H): 281.1. found: 281.1.

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe excess phosphoryl chloride was removed by vacuum distillation
  3. additionThe residue was diluted with ice-water
  4. extractionextracted with DCM three times
  5. customThe combined organic layers were dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d90cc6423a5d4b6dbce8a3fc38653539
Source dataset
uspto-grants-2011_01
Patent number
US07863285B2

Reaction notes

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