Phosphorus oxychloride → 6-chloro-8-methyl-1H-purine

HRID 243332Notes

Reaction equation

HRID 243332 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][NH:5][C:6](=O)[C:7]=1[NH:8][C:9](=O)[CH3:10].P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:6]1[N:5]=[CH:4][N:3]=[C:2]2[C:7]=1[N:8]=[C:9]([CH3:10])[NH:1]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135441457N-(4-Amino-6-oxo-1,6-dihydropyrimidin-5-YL)acetamide

Product 1

HCID 1784322486-chloro-8-methyl-1H-purineYield 6%

Procedure

A solution of N-(4-amino-6-oxo-1,6-dihydropyrimidin-5-yl)acetamide (330 mg, 1.92 mmol, 1.00 equiv, 98%) in phosphorus oxychloride (5 mL) was refluxed overnight. The resulting mixture was concentrated under vacuum. The residue was redissolved in 10 mL of ethyl acetate, washed with 10 mL of saturated aqueous sodium bicarbonate solution, 1×10 mL of water and 1×10 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum to give 20 mg (6%) of 6-chloro-8-methyl-9H-purine as a yellow solid.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. dissolutionThe residue was redissolved in 10 mL of ethyl acetate
  3. washwashed with 10 mL of saturated aqueous sodium bicarbonate solution, 1×10 mL of water and 1×10 mL of brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2bda3759cb194fe8addbdf81abeca081
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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