Ethyl bromoacetate → HCID 12944784, compound

HRID 894830Notes

Reaction equation

HRID 894830 reaction equation
[Cl:1][C:2]1[NH:3][CH2:4][C:5]2[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:6]=2[N:7]=1.Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[Cl:1][C:2]1[N:3]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:4][C:5]2[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 178435023HCID 178435023, compound

Product 1

HCID 12944784HCID 12944784, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 6.0 g of 2-chloro-5,6-dimethyl-3,4-dihydrothieno[2,3-d]pyrimidine, 5.52 g of ethyl bromoacetate and 12.5 g of powdered potassium carbonate in 300 ml of methyl ethyl ketone was heat-refluxed with stirring under a nitrogen atmosphere for 4 hours. After cooling, an insoluble inorganic salt was filtered off and the filtrate was concentrated in vacuo to give a crude oil of 2-chloro-3-ethoxycarbonylmethyl-5,6-dimethyl-3,4-dihydrothieno[2,3-d]pyrimidine. Because of the instability of the resulting compound, the crude oil was used in the subsequent reaction.

Workup

  1. temperaturewas heat-refluxed
  2. temperatureAfter cooling
  3. filtrationan insoluble inorganic salt was filtered off
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2b8aa6fd3bf641ffa36e028d13464eed
Source dataset
uspto-grants-1981_08
Patent number
US04284773

Reaction notes

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