4,5,6-Trichloro-2-methylpyrimidine → HCID 15003621, compound

HRID 2278503Notes

Reaction equation

HRID 2278503 reaction equation
[CH3:1][O-:2].[Na+].[CH3:4][C:5]1[N:10]=[C:9](Cl)[C:8]([Cl:12])=[C:7]([Cl:13])[N:6]=1>C1COCC1>[Cl:13][C:7]1[C:8]([Cl:12])=[C:9]([O:2][CH3:1])[N:10]=[C:5]([CH3:4])[N:6]=1

Participants

4

Reactant 2

HCID 2310544,5,6-Trichloro-2-methylpyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 15003621HCID 15003621, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

1.37 g of sodium methoxide are added to a solution of 5 g of 2-methyl-4,5,6-trichloropyrimidine in 41 ml of THF cooled to 5° C. in an ice bath. The ice bath is removed. The suspension is stirred at ambient temperature for 18 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 so as to give 4.73 g of 4,5-dichloro-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 so as

Sources & evidence

ORD record
ord-9879af4a3e9f413faeb4d7b3182b496b
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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