2-[4-(4-Acetoxybenzoyl)benzylthio]-3,5-dimethylthieno[2,3-d]pyrimidin-4(3H)-one → 3,5-dimethyl-2-[4-(4-hydroxybenzoyl)benzylthio]thieno[2,3-d]pyrimidin-4(3H)-one

HRID 1291340Notes

Reaction equation

HRID 1291340 reaction equation
C([O:4][C:5]1[CH:32]=[CH:31][C:8]([C:9]([C:11]2[CH:30]=[CH:29][C:14]([CH2:15][S:16][C:17]3[N:18]([CH3:28])[C:19](=[O:27])[C:20]4[C:25]([CH3:26])=[CH:24][S:23][C:21]=4[N:22]=3)=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+].O>O1CCCC1>[CH3:28][N:18]1[C:19](=[O:27])[C:20]2[C:25]([CH3:26])=[CH:24][S:23][C:21]=2[N:22]=[C:17]1[S:16][CH2:15][C:14]1[CH:13]=[CH:12][C:11]([C:9](=[O:10])[C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:32][CH:31]=2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 189192392-[4-(4-Acetoxybenzoyl)benzylthio]-3,5-dimethylthieno[2,3-d]pyrimidin-4(3H)-oneHCID 23719242Sodium hydroxide--water (1/1/1)

Product 1

HCID 189188093,5-dimethyl-2-[4-(4-hydroxybenzoyl)benzylthio]thieno[2,3-d]pyrimidin-4(3H)-oneYield 60.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[4-(4-acetoxybenzoyl)benzylthio]-3,5-dimethylthieno [2,3-d]pyrimidin-4(3H)-one (1.40 g) and 1N-sodium hydroxide/water (6.7 ml) in tetrahydrofuran (20 ml) was stirred at room temperature for 10 minutes. This reaction mixture was concentrated and the residue was dissolved in water and acidified with 1N-HCl. The resulting precipitate was extracted with ethyl acetate, washed with water, dried, and concentrated. The residue was recrystallized from methanol-ethyl acetate to provide the title compound as colorless solid (775 mg).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in water
  3. extractionThe resulting precipitate was extracted with ethyl acetate
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-ad1d5983f0db4483a923af585f431b90
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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