Ethyl bromoacetate → HCID 10364000, compound

HRID 1198925Notes

Reaction equation

HRID 1198925 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]3[C:14]([CH3:18])=[C:15]([CH3:17])[S:16][C:10]=3[NH:9][C:8]2=[O:19])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:12](=[O:13])[C:11]3[C:14]([CH3:18])=[C:15]([CH3:17])[S:16][C:10]=3[N:9]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:8]2=[O:19])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 10471279HCID 10471279, compound

Product 1

HCID 10364000HCID 10364000, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 0.6 g quantity of 3-(4-chlorobenzyl)-5,6-dimethylthieno[2,3-d]pyrimidin-2,4(1H,3H)-dione (Compound III-1) was dissolved in 20 ml of anhydrous N,N-dimethylformamide. To the solution were added at room temperature 0.1 g of 50% sodium hydride and then 0.4 g of ethyl bromoacetate. The mixture was stirred at room temperature for 17 hours, concentrated and acidified by adding diluted hydrochloric acid with ice-cooling. The crystals precipitated were collected by filtration and recrystallized from ethanol, giving 0.7 g of 3-(4-chlorobenzyl)-1-ethoxycarbonylmethyl-5,6-dimethylthieno[2,3-d]pyrimidin-2,4(1H,3H)-dione having a melting point of 151° to 152° C. in a yield of 92%.

Workup

  1. concentrationconcentrated
  2. additionby adding diluted hydrochloric acid with ice-
  3. temperaturecooling
  4. customThe crystals precipitated
  5. filtrationwere collected by filtration
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f86a30cee56b4dce8939f9992eabe71b
Source dataset
uspto-grants-1990_02
Patent number
US04898867

Reaction notes

Loading…