Phosphorus oxychloride → 4-Chloro-5-methyl-6-(1-methylethyl)pyrimidine

HRID 241003Notes

Reaction equation

HRID 241003 reaction equation
[CH:1]([C:4]1[N:9]=[CH:8][N:7]=[C:6](O)[C:5]=1[CH3:11])([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:6]1[C:5]([CH3:11])=[C:4]([CH:1]([CH3:3])[CH3:2])[N:9]=[CH:8][N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178431782HCID 178431782, compound

Product 1

HCID 583334224-Chloro-5-methyl-6-(1-methylethyl)pyrimidineYield 11%

Conditions

Temperature
70 °C

Procedure

To 6-isopropyl-5-methylpyrimidin-4-ol (0.25 g, 1.6 mmol) was added neat phosphorous oxychloride (5 mL) and the mixture stirred at 70° C. for 3 h. After cooling to room temperature the solution was concentrated, diluted with water then neutralized by portionwise addition of saturated sodium carbonate solution. The aqueous mixture was extracted with ethyl acetate and the organic solution washed with brine then dried over anhydrous sodium sulfate. Filtration and concentration provided 4-chloro-6-isopropyl-5-methylpyrimidine (30 mg, 11% yield) as a brown oil that was used without further purification. MS (EI) for C8H11ClN2: 170 (MH+).

Workup

  1. temperatureAfter cooling to room temperature the solution
  2. concentrationwas concentrated
  3. additiondiluted with water
  4. additionthen neutralized by portionwise addition of saturated sodium carbonate solution
  5. extractionThe aqueous mixture was extracted with ethyl acetate
  6. washthe organic solution washed with brine
  7. dry with materialthen dried over anhydrous sodium sulfate
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-53cb32f2356f43268d46889e27b342df
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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