Hydrochloric Acid → 5-Methyl-4-oxo-2-(thiophen-3-ylmethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid

HRID 388405

Reaction equation

HRID 388405 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7]([CH2:12][C:13]3[CH:17]=[CH:16][S:15][CH:14]=3)=[N:6][C:5]=2[S:4][C:3]=1[C:18]([O:20]CC)=[O:19].[OH-].[Na+].Cl>C(O)C>[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7]([CH2:12][C:13]3[CH:17]=[CH:16][S:15][CH:14]=3)=[N:6][C:5]=2[S:4][C:3]=1[C:18]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68664667Ethyl 5-methyl-4-oxo-2-(thiophen-3-ylmethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 160910835-Methyl-4-oxo-2-(thiophen-3-ylmethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acidYield 92.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 379 mg of ethyl 5-methyl-4-oxo-2-(thiophen-3-ylmethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate as synthesized in Production Example 1, 3.4 mL of 1N aqueous sodium hydroxide solution and 2.2 mL of ethanol was heated under reflux for 2 hours. After cooling off, the reaction liquid was poured on ice, rendered acidic with diluted hydrochloric acid, and the precipitated crystals were recovered by filtration. After washing with water, the crystals were dried by heating under reduced pressure, to provide 320 mg of 5-methyl-4-oxo-2-(thiophen-3-ylmethyl)-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling off
  4. customthe reaction liquid
  5. additionwas poured on ice
  6. filtrationthe precipitated crystals were recovered by filtration
  7. washAfter washing with water
  8. customthe crystals were dried
  9. temperatureby heating under reduced pressure

Sources & evidence

ORD record
ord-bdef864c039d47bc9d99340187e10c79
Source dataset
uspto-grants-2013_02
Patent number
US08377944B2

Linked notes

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