Sodium Methoxide → Methyl 2-(4-chloro-6-methoxypyrimidin-5-yl)acetate

HRID 1078189Notes

Reaction equation

HRID 1078189 reaction equation
[CH3:1][O-:2].[Na+].[Cl:4][C:5]1[C:10]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:9](Cl)[N:8]=[CH:7][N:6]=1>CO.COCCOC>[Cl:4][C:5]1[C:10]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:9]([O:2][CH3:1])[N:8]=[CH:7][N:6]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 54165419Methyl 2-(4,6-dichloropyrimidin-5-yl)acetate

Product 1

HCID 54047637Methyl 2-(4-chloro-6-methoxypyrimidin-5-yl)acetate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium methylate in methanol (112 ml of a 5.4 molar solution) is added at room temperature to a solution of methyl 4,6-dichloro-pyrimidin-5-yl-acetate (120 g, 0.54 mol) in 1,2-dimethoxyethane (200 ml) with cooling. The reaction mixture is stirred for 30 minutes and poured on crushed ice. The precipitated crystals are filtered and dried to give the methyl 4-chloro-6-methoxy-pyrimidin-5-yl-acetate (106 g), m.p. 64° C.

Workup

  1. temperaturewith cooling
  2. additionpoured
  3. customon crushed ice
  4. filtrationThe precipitated crystals are filtered
  5. customdried

Sources & evidence

ORD record
ord-94e2970a1e94430d83a8a9fb33043002
Source dataset
uspto-grants-1996_08
Patent number
US05547919

Reaction notes

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