Ethyl Acetate → Ethyl 2-(4-chloro-6-methoxypyrimidin-2-yl)acetate

HRID 2278581Notes

Reaction equation

HRID 2278581 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl[C:12]1[N:17]=[C:16]([Cl:18])[CH:15]=[C:14]([O:19][CH3:20])[N:13]=1.[C:21]([O:24][CH2:25][CH3:26])(=[O:23])[CH3:22]>C1COCC1>[CH2:25]([O:24][C:21](=[O:23])[CH2:22][C:12]1[N:17]=[C:16]([Cl:18])[CH:15]=[C:14]([O:19][CH3:20])[N:13]=1)[CH3:26]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2733832Lithium HexamethyldisilazideHCID 38245092,4-Dichloro-6-methoxypyrimidine

Product 1

HCID 86699270Ethyl 2-(4-chloro-6-methoxypyrimidin-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-75 °C

Procedure

91.4 ml of 1M lithium bis(trimethylsilyl)amide (THF) are added dropwise to a solution of 7.4 g of 2,4-dichloro-6-methoxypyrimidine and 4.5 ml of ethyl acetate in 100 ml of anhydrous THF cooled to −75° C. in a dry ice/acetone bath. The reaction medium is stirred at −75° C. for one hour. The cooling bath is removed so as to allow the temperature to rise to 22° C. The reaction medium is stirred at 22° C. for one hour. 100 ml of water and 400 ml of ethyl acetate are added. After settling out, the organic phase is dried over magnesium sulfate, filtered, and then concentrated under reduced pressure so as to give 9.5 g of (4-chloro-6-methoxypyrimidin-2-yl)acetic acid ethyl ester in the form of an orange oil, the characteristics of which are the following:

Workup

  1. customThe cooling bath is removed so as
  2. customto rise to 22° C
  3. stirringThe reaction medium is stirred at 22° C. for one hour
  4. addition100 ml of water and 400 ml of ethyl acetate are added
  5. dry with materialthe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure so as

Sources & evidence

ORD record
ord-9f2c058dfccb480a84a97f2c9a65b736
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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