Dimethyl Sulfate → HCID 53945577, compound

HRID 1957174Notes

Reaction equation

HRID 1957174 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[O:7][C:8]1[C:13]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:12]([O:19][CH3:20])[N:11]=[C:10]([CH3:21])[N:9]=1)([CH3:3])[CH3:2].[H-].[Na+].COS(OC)(=O)=O.[CH3:34][O:35][CH2:36]COC>C(CNCC=O)=O.CN(C=O)C>[CH:1]([C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[O:7][C:8]1[C:13]([C:14](=[CH:34][O:35][CH3:36])[C:15]([O:17][CH3:18])=[O:16])=[C:12]([O:19][CH3:20])[N:11]=[C:10]([CH3:21])[N:9]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 53760831HCID 53760831, compound

Product 1

HCID 53945577HCID 53945577, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 202686642,2'-AzanediyldiacetaldehydeSolvent

Procedure

A solution of methyl 4-(3-isopropylphenoxy)-6-methoxy-2-methyl-pyrimidin-5-yl-acetate (8.6 g, 26 mol) in 1,2-dimethoxyethane (20 ml) and N,N-diformylmethylamine (8 ml) is added at 5° C. to a suspension of NaH (1.6 g, 80% in oil, 52 mol) in DMF (30 ml). The mixture is stirred for 4 hours at room temperature. Dimethylsulfate (3.7 ml, 39 mol) is added at 0° C. and stirring is continued for 3 hours. Dilution with ether, washing with brine and chromatography on silicagel (eluent hexane/ethyl acetate 3:1) gives methyl α-[4-(3-isopropylphenoxy)-6-methoxy-2-methyl-pyrimidin-5-yl]-β-methoxyacrylate as a colorless oil (7.2 g, 74%).

Workup

  1. stirringstirring
  2. waitis continued for 3 hours
  3. washDilution with ether, washing with brine and chromatography on silicagel (eluent hexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-8c45c046de83440dba0edcc877383553
Source dataset
uspto-grants-1998_07
Patent number
US05783580

Reaction notes

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