Methanol → Methyl 2-(4,6-dimethoxypyrimidin-2-yl)oxybut-2-enoate

HRID 847119

Reaction equation

HRID 847119 reaction equation
[OH:1][CH:2]([CH:7]=[CH2:8])[C:3]([O:5][CH3:6])=[O:4].[CH3:9][O:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[N:14]=[C:13](S(C)(=O)=O)[N:12]=1.C(=O)([O-])[O-].[K+].[K+].CO>C(C(C)=O)C.C(Cl)(Cl)Cl>[CH3:9][O:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[N:14]=[C:13]([O:1][C:2](=[CH:7][CH3:8])[C:3]([O:5][CH3:6])=[O:4])[N:12]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 545123Methyl 2-hydroxybut-3-enoateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidine

Product 1

HCID 53952661Methyl 2-(4,6-dimethoxypyrimidin-2-yl)oxybut-2-enoateYield 78.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of methyl 2-hydroxybut-3-enoate (0.80g, 6.9mmol), 4,6-dimethoxy-2-methanesulphonylpyrimidine (1.50g, 6.9mmol) and potassium carbonate (1.04g, 7.6mmol) in methyl ethyl ketone (100ml) was refluxed for 12 hours. The reaction mixture was filtered and the filtrate evaporated in vacuo. Flash column chromatography (silica, 1.5% methanol in chloroform) of the residue gave the title compound (1.37g, 78% yield by weight).

Workup

  1. temperaturewas refluxed for 12 hours
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-926200faf6b44bfaa25326ff0c79f915
Source dataset
uspto-grants-1992_08
Patent number
US05139563

Linked notes

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