Triethylamine → Ethyl 2-methyl-4-(3,4-dimethoxyphenyl)-5-pyrimidinecarboxylate

HRID 4679

Reaction equation

HRID 4679 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:6]([C:8](=[CH:14]N(C)C)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=O.Cl.[C:24]([NH2:27])(=[NH:26])[CH3:25].C(N(CC)CC)C>C(O)C>[CH3:25][C:24]1[N:27]=[C:6]([C:5]2[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:14][N:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67170Acetamidine monohydrochlorideHCID 53710889Ethyl 2-(3,4-dimethoxybenzoyl)-2-(dimethylaminomethylene)acetate

Product 1

HCID 20151431Ethyl 2-methyl-4-(3,4-dimethoxyphenyl)-5-pyrimidinecarboxylateYield 45.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-(3,4-dimethoxybenzoyl)-2-(dimethylaminomethylene)acetate (31 g), acetoamidine hydrochloride (13.3 g) and triethylamine (16.2 g) in ethanol (200 ml) was refluxed for 10 hours under stirring. The reaction mixture was evaporated in vacuo and the residue was dissolved in a mixture of ethyl acetate and water. The separatedorganic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from ethyl ether to give ethyl 2-methyl-4-(3,4-dimethoxyphenyl)-5-pyrimidinecarboxylate (14 g).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate and water
  3. washThe separatedorganic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was crystallized from ethyl ether

Sources & evidence

ORD record
ord-341f97577ef543daa52fec737b242a18
Source dataset
uspto-grants-1988_02
Patent number
US04727073

Linked notes

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