Dimethyl Sulfate → Methyl alpha-[4-(3-methylphenoxy)-6-methoxy-pyrimidin-5-yl)-beta-methoxyacrylate

HRID 1957164Notes

Reaction equation

HRID 1957164 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[O:5][C:6]1[C:11]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[C:10]([O:17][CH3:18])[N:9]=[CH:8][N:7]=1.[H-].[Na+].COS(OC)(=O)=O.[CH3:31][O:32][CH2:33]COC>C(OC)=O.CCOCC>[CH3:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[O:5][C:6]1[C:11]([C:12](=[CH:31][O:32][CH3:33])[C:13]([O:15][CH3:16])=[O:14])=[C:10]([O:17][CH3:18])[N:9]=[CH:8][N:7]=1

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 54458061Methyl 4-(3-methylphenoxy)-6-methoxy-pyrimidin-5-yl-acetate

Product 1

HCID 57241123Methyl alpha-[4-(3-methylphenoxy)-6-methoxy-pyrimidin-5-yl)-beta-methoxyacrylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 7865Methyl formateSolvent

Procedure

Methyl 4-(3-methylphenoxy)-6-methoxy-pyrimidin-5-yl-acetate (12.1 g, 42 mmol) is dissolved in a mixture of 1,2-dimethoxyethane (120 ml) and methyl formate (50 ml). Sodium hydride (2.5 g, 80% in oil, 84 mmol) is added in one portion, the temperature being kept at room temperature. After 5 hours dimethylsulfate (6.6 ml, 70 mmol) is added with cooling. After an additional 5 hours the reaction mixture is diluted with ether and washed with brine. Drying and chromatography on silicagel (eluant:hexane/ethyl acetate 1:1) gives the E-isomer of methyl α-[4-(3-methylphenoxy)-6-methoxy-pyrimidin-5-yl)-β-methoxyacrylate as a crystalline solid, m.p. 107° C.

Workup

  1. custombeing kept at room temperature
  2. temperaturewith cooling
  3. washwashed with brine
  4. customDrying

Sources & evidence

ORD record
ord-cf38aacbdd174d17ad433c927bcab75d
Source dataset
uspto-grants-1998_07
Patent number
US05783580

Reaction notes

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