Sodium Methoxide → HCID 84819874, compound

HRID 2278479Notes

Reaction equation

HRID 2278479 reaction equation
[CH3:1][O-:2].[Na+].[CH3:4][C:5]1[N:10]=[C:9](Cl)[C:8]([F:12])=[C:7]([Cl:13])[N:6]=1>C1COCC1>[Cl:13][C:7]1[C:8]([F:12])=[C:9]([O:2][CH3:1])[N:10]=[C:5]([CH3:4])[N:6]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 137310334,6-Dichloro-5-fluoro-2-methylpyrimidine

Product 1

HCID 84819874HCID 84819874, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

3.21 g of sodium methoxide are added to a solution of 9.8 g of 2-methyl-4,6-dichloro-5-fluoropyrimidine in 80 ml of THF cooled to 5° C. in an ice bath. The ice bath is removed. The suspension is stirred at ambient temperature for 3 hours. The reaction medium is cooled to 5° C. in an ice bath. 20 ml of water and 100 ml of ethyl acetate are added. After settling out, the organic phase is dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give 9 g of 4-chloro-5-fluoro-6-methoxy-2-methylpyrimidine in the form of a colorless oil which crystallizes, the characteristics of which are the following:

Workup

  1. customThe ice bath is removed
  2. temperatureThe reaction medium is cooled to 5° C. in an ice bath
  3. addition20 ml of water and 100 ml of ethyl acetate are added
  4. dry with materialthe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-35a2bec9d07c4dce81212672b69bc1e1
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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