Diethyl Ether → Methyl alpha-[4-methyl-6-(3-phenylphenoxy)-5-pyrimidinyl]-beta-dimethylaminoacrylate

HRID 2400128Notes

Reaction equation

HRID 2400128 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:10]=2)[C:3]=1[CH2:21][C:22]([O:24][CH3:25])=[O:23].CC([O-])(C)C.[K+].[CH3:32][N:33]([CH3:36])[CH:34]=O.S(OC)(OC)(=O)=O.CCOCC>COCCOC>[CH3:1][C:2]1[C:3]([C:21](=[CH:32][N:33]([CH3:36])[CH3:34])[C:22]([O:24][CH3:25])=[O:23])=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:10]=2)[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11127270DMF dimethylsulfateHCID 19044665Methyl [6-methyl-4-(3-phenylphenoxy)-5-pyrimidinyl]-acetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 53660927Methyl alpha-[4-methyl-6-(3-phenylphenoxy)-5-pyrimidinyl]-beta-dimethylaminoacrylateYield 95%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Methyl [6-methyl-4-(3-phenylphenoxy)-5-pyrimidinyl]-acetate (60 g, 0.18 mol) is added in one portion to a solution of t-BuOK (60 g, 0.53 mol) in 1,2-dimethoxyethane (0.51) at -40° C. After 1 hour dimethylformamide-dimethyl sulfate (1:1 adduct, 120 ml) is added at -50° C. The reaction mixture is allowed to warm to room temperature to give a yellow suspension. Addition of ether, washing repeatedly with brine and drying gives the crude methyl α-[4-methyl-6-(3-phenylphenoxy)-5-pyrimidinyl]-β-dimethylaminoacrylate (67 g, 95%) as an oil.

Workup

  1. customto give a yellow suspension
  2. washwashing repeatedly with brine
  3. customdrying

Sources & evidence

ORD record
ord-776c5b74d3cb4e1f81d2575bf91e6d7e
Source dataset
uspto-grants-1995_09
Patent number
US05453427

Reaction notes

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