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

HRID 600579Notes

Reaction equation

HRID 600579 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-c9535860a95944609efd2acdb51b003c
Source dataset
uspto-grants-2011_03
Patent number
US07902205B2

Reaction notes

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