Methanol → 4-Chloro-2-methoxy-6-methylpyrimidine

HRID 333066Notes

Reaction equation

HRID 333066 reaction equation
[Na].Cl[C:3]1[N:8]=[C:7]([Cl:9])[CH:6]=[C:5]([CH3:10])[N:4]=1.[OH2:11].[CH3:12]O>>[Cl:9][C:7]1[CH:6]=[C:5]([CH3:10])[N:4]=[C:3]([O:11][CH3:12])[N:8]=1

Participants

5

Reactant 4

HCID 887Methanol2×HCID 962WaterHCID 794712,4-Dichloro-6-methylpyrimidineHCID 5360545Sodium

Product 1

HCID 134258364-Chloro-2-methoxy-6-methylpyrimidine

Procedure

To anhydrous methanol (10 ml) was added sodium (230 mg, 10 mmol) and the mixture was stirred under an argon atmosphere until a clear solution had formed. This solution was added dropwise over two hours with stirring to a solution of 2,4-dichloro-6-methylpyrimidine (1.79 g, 11 mmol) in anhydrous methanol (10 ml) under cooling so that the temperature remained below 10° C. Stirring was continued for 30 minutes, then water was added (2 ml), the mixture was filtered and the filtrate was evaporated to dryness under reduced pressure. The residue was purified by column chromatography (pre-packed silica column, gradient of heptane/ethyl acetate). 750 mg was obtained (4.75 mmol, 47%). MS (APCI) m/z=159.2 [M+H]+.

Workup

  1. customhad formed
  2. additionThis solution was added dropwise over two hours
  3. temperatureunder cooling so that the temperature
  4. customremained below 10° C
  5. stirringStirring
  6. filtrationthe mixture was filtered
  7. customthe filtrate was evaporated to dryness under reduced pressure
  8. customThe residue was purified by column chromatography (pre-packed silica column, gradient of heptane/ethyl acetate)
  9. custom750 mg was obtained (4.75 mmol, 47%)

Sources & evidence

ORD record
ord-ff1bbdd973f8423086e675f8be01fd11
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Reaction notes

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