Hydrochloric Acid → (4-Oxo-5-phenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)acetic acid ethyl ester

HRID 910190Notes

Reaction equation

HRID 910190 reaction equation
Cl.C(O[C:5]([C:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][S:9][C:8]=1[NH2:18])=[O:6])C.[C:19]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])#[N:20]>>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][C:19]1[NH:20][C:5](=[O:6])[C:7]2[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:10][S:9][C:8]=2[N:18]=1)[CH3:26]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 73242Ethyl 2-amino-4-phenylthiophene-3-carboxylate

Product 1

HCID 13591037(4-Oxo-5-phenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)acetic acid ethyl ester

Procedure

Hydrogen chloride gas was bubbled through a stirred reaction mixture of 2-amino-4-phenylthiophene-3-carboxylic acid ethyl ester (4.94 g, 0.02 mol) in ethyl cyanoacetate (50 ml) for 2 hours. A thick suspension formed initially which slowly dissolved on gentle warming. The mixture was allowed to stand at ambient temperature for 18 hours. Excess hydrogen chloride was removed by bubbling nitrogen through the reaction mixture and most of the excess ethyl cyanoacetate was distilled out at reduced pressure. The solid residue was recrystallised from ethanol to give (4-oxo-5-phenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)acetic acid ethyl ester (3.64 g), which was used without further purification.

Workup

  1. customA thick suspension formed initially which
  2. dissolutionslowly dissolved on gentle warming
  3. customExcess hydrogen chloride was removed
  4. customby bubbling nitrogen through the reaction mixture
  5. distillationmost of the excess ethyl cyanoacetate was distilled out at reduced pressure
  6. customThe solid residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-457976e48af84b58be99428e99557f5e
Source dataset
uspto-grants-2011_09
Patent number
US08022076B2

Reaction notes

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