Ethyl bromoacetate → HCID 13608185, compound

HRID 1905875Notes

Reaction equation

HRID 1905875 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[NH:16][C:15](=[O:17])[N:14]([CH3:18])[C:13](=[N:19][C:20]3[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=3[CH3:28])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CC(C)([O-])C.[K+].Br[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]([CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:15](=[O:17])[N:14]([CH3:18])[C:13](=[N:19][C:20]3[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=3[CH3:28])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 23665647Potassium tert-butoxideHCID 178418505HCID 178418505, compound

Product 1

HCID 13608185HCID 13608185, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)-2(1H)-pyrimidinone (26.1 g) in N,N-dimethylformamide (350 ml) were added potassium tert. butoxide (9.2 g) and ethyl bromoacetate (13.7 g) at room temperature. The mixture was stirred overnight. After neutralization with diluted hydrochloric acid, the mixture was evaporated and chromatographed on silica gel using chloroform. Fractions containing the object compound were evaporated and the residue was triturated in ethanol to give 3,4-dihydro-6-(3,4-dimethoxyphenyl)-1-ethoxycarbonylmethyl-methyl-4(2,4,6-trimethylphenylimino)-2(1H)pyrimidinone (15.3 g). mp. 112°-113° C.

Workup

  1. customAfter neutralization with diluted hydrochloric acid, the mixture was evaporated
  2. customchromatographed on silica gel
  3. additionFractions containing the object compound
  4. customwere evaporated
  5. customthe residue was triturated in ethanol

Sources & evidence

ORD record
ord-c8fedef12f4a4eabbfdec8b501a76c5e
Source dataset
uspto-grants-1987_03
Patent number
US04649142

Reaction notes

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