Water → 5-methyl-4-oxo-3H,4H-thieno[2,3-d]pyrimidine-6-carboxylic acid

HRID 1094713Notes

Reaction equation

HRID 1094713 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][CH:7]=[N:6][C:5]=2[S:4][C:3]=1[C:12]([O:14]CC)=[O:13].O.O.[OH-].[Li+]>C1COCC1.CO>[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][CH:7]=[N:6][C:5]=2[S:4][C:3]=1[C:12]([OH:14])=[O:13]

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 731240Ethyl 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 4058025-methyl-4-oxo-3H,4H-thieno[2,3-d]pyrimidine-6-carboxylic acidYield 95.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate (1.0 g, 4.5 mmol) in THF (14 mL), MeOH (3 mL), and H2O (3 mL) was added lithium hydroxide monohydrate (0.68 g, 16 mmol). The reaction mixture was stirred at RT overnight. The reaction mixture was concentrated, diluted with H2O (20 mL) and washed with DCM (25 mL). The aqueous layer was acidified (pH˜2) with 1M HCl and the resultant precipitate was filtered and dried to give 0.9 g of pure 5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid, (yield: 94%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with H2O (20 mL)
  3. washwashed with DCM (25 mL)
  4. filtrationthe resultant precipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-a5e9a7d013ec4dcebac3b9b7af87332f
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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