Phosphorus oxychloride → HCID 59598569, compound

HRID 81766Notes

Reaction equation

HRID 81766 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=O)[C:5]([O:9][C:10]2[CH:15]=[C:14]([CH3:16])[C:13]([O:17][CH3:18])=[CH:12][C:11]=2[CH:19]([CH3:21])[CH3:20])=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:6]1[C:5]([O:9][C:10]2[CH:15]=[C:14]([CH3:16])[C:13]([O:17][CH3:18])=[CH:12][C:11]=2[CH:19]([CH3:21])[CH3:20])=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 595985922-amino-5-(2-isopropyl-4-methoxy-5-methyl-phenoxy)-3H-pyrimidin-4-one

Product 1

HCID 59598569HCID 59598569, compoundYield 88%

Conditions

Temperature
110 °C

Procedure

A mixture of 2-amino-5-(2-isopropyl-4-methoxy-5-methyl-phenoxy)-3H-pyrimidin-4-one in phosphorus oxychloride (5 ml) was heated at 110° C. for 40 minutes and stirred at room temperature over night. Solvent was removed under reduced pressure and ice water was added. The aqueous solution was basified with potassium carbonate to pH 9, and extracted with methylene chloride. The organic phase was washed with brine and dried over anhydrous sodium sulfate. After removal of drying agent, the organic solution was concentrated under reduced pressure to yield 4-chloro-5-(2-isopropyl-4-methoxy-5-methyl-phenoxy)-pyrimidin-2-ylamine as yellow solid (0.043 g, 88%). MS M+H=308.

Workup

  1. customSolvent was removed under reduced pressure and ice water
  2. additionwas added
  3. extractionextracted with methylene chloride
  4. washThe organic phase was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter removal
  7. customof drying agent
  8. concentrationthe organic solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0e860d4805b54e9e99cb2bbaab00d522
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Reaction notes

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