Acetonitrile → 2-Chloro-4-[1-(methoxycarbonyl)ethoxy]pyrimidine

HRID 1862223Notes

Reaction equation

HRID 1862223 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[CH:2]([CH3:4])[OH:3].C(#N)C.[H-].[Na+].[Cl:13][C:14]1[N:19]=[C:18]([Cl:20])[CH:17]=[CH:16][N:15]=1>O>[Cl:13][C:14]1[N:19]=[C:18]([O:3][CH:2]([C:1]([O:6][CH3:7])=[O:5])[CH3:4])[CH:17]=[CH:16][N:15]=1.[Cl:20][C:18]1[CH:17]=[CH:16][N:15]=[C:14]([O:3][CH:2]([C:1]([O:6][CH3:7])=[O:5])[CH3:4])[N:19]=1

Participants

7

Reactant 4

HCID 6342Acetonitrile3×HCID 11040Methyl LactateHCID 24758Sodium hydrideHCID 775312,4-Dichloropyrimidine

Product 2

HCID 120567412-Chloro-4-[1-(methoxycarbonyl)ethoxy]pyrimidineHCID 120567434-Chloro-2-[1-(methoxycarbonyl)ethoxy]pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.12 g of methyl lactate and 10 ml of acetonitrile was added to a mixture of 1.2 g of sodium hydride and 40 ml of acetonitrile dropwise under ice cooling, and the mixture was stirred for 30 minutes. To this was added a mixture of 4.47 g of 2,4-dichloropyrimidine and 10 ml of acetonitrile dropwise at the same temperature, and the mixture was stirred at 60° C. for 2 hours. This reaction solution was cooled to room temperature, then, poured into water, and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 2.5 g of 2-chloro-4-[1-(methoxycarbonyl)ethoxy]pyrimidine and 0.25 g of 4-chloro-2-[1-(methoxycarbonyl)ethoxy]pyrimidine. 2-Chloro-4-[1-(methoxycarbonyl)ethoxy]pyrimidine

Workup

  1. additionTo this was added
  2. stirringthe mixture was stirred at 60° C. for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ef66615ff5534e9aa640fff2332b2a6f
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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