2-[4-(4-acetoxybenzoyl) benzylthio]-3-methylthieno[3,2-d]pyrimidin-4(3H)-one → 2-[4-(4-hydroxybenzoyl)benzylthio]-3-methylthieno[3,2-d]pyrimidin-4(3H)-one

HRID 1291345Notes

Reaction equation

HRID 1291345 reaction equation
C([O:4][C:5]1[CH:31]=[CH:30][C:8]([C:9]([C:11]2[CH:29]=[CH:28][C:14]([CH2:15][S:16][C:17]3[N:18]([CH3:27])[C:19](=[O:26])[C:20]4[S:25][CH:24]=[CH:23][C:21]=4[N:22]=3)=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+].O>C1COCC1>[OH:4][C:5]1[CH:31]=[CH:30][C:8]([C:9]([C:11]2[CH:29]=[CH:28][C:14]([CH2:15][S:16][C:17]3[N:18]([CH3:27])[C:19](=[O:26])[C:20]4[S:25][CH:24]=[CH:23][C:21]=4[N:22]=3)=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 189192362-[4-(4-acetoxybenzoyl) benzylthio]-3-methylthieno[3,2-d]pyrimidin-4(3H)-oneHCID 23719242Sodium hydroxide--water (1/1/1)

Product 1

HCID 189189232-[4-(4-hydroxybenzoyl)benzylthio]-3-methylthieno[3,2-d]pyrimidin-4(3H)-oneYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[4-(4-acetoxybenzoyl) benzylthio]-3-methylthieno[3,2-d]pyrimidin-4(3H)-one (3.51 g) in THF (20 ml) was added 1N-sodium hydroxide/water (10 ml) and the mixture was stirred at room temperature for 30 minutes. This reaction mixture was concentrated, the residue was dissolved in water, and 1N-hydrochloric acid was added. The resulting crystals were collected by filtration, rinsed with water, and dried to provide the title compound as colorless solid (3.22 g).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in water
  3. addition1N-hydrochloric acid was added
  4. filtrationThe resulting crystals were collected by filtration
  5. washrinsed with water
  6. customdried

Sources & evidence

ORD record
ord-ad72acb3032f4514bc942a9b1a7568b9
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

Loading…