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

HRID 1291344Notes

Reaction equation

HRID 1291344 reaction equation
[SH:1][C:2]1[N:3]([CH3:12])[C:4](=[O:11])[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[OH-].[Na+].O.[C:16]([O:19][C:20]1[CH:35]=[CH:34][C:23]([C:24]([C:26]2[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=2)=[O:25])=[CH:22][CH:21]=1)(=[O:18])[CH3:17]>C(O)C.O>[C:16]([O:19][C:20]1[CH:35]=[CH:34][C:23]([C:24]([C:26]2[CH:27]=[CH:28][C:29]([CH2:30][S:1][C:2]3[N:3]([CH3:12])[C:4](=[O:11])[C:5]4[S:10][CH:9]=[CH:8][C:6]=4[N:7]=3)=[CH:32][CH:33]=2)=[O:25])=[CH:22][CH:21]=1)(=[O:18])[CH3:17]

Participants

6

Reactant 3

HCID 189192074-(4-Acetoxybenzoyl)benzyl bromideHCID 23719242Sodium hydroxide--water (1/1/1)HCID 178481668HCID 178481668, compound

Product 1

HCID 189192362-[4-(4-acetoxybenzoyl) benzylthio]-3-methylthieno[3,2-d]pyrimidin-4(3H)-oneYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-mercapto-3-methylthieno[3,2-d]-pyrimidin-4(3H)-one (1.98 g) and 1N-sodium hydroxide/water (10 ml) in ethanol (30 ml) was added 4-(4-acetoxybenzoyl)benzyl bromide (3.95 g) and the mixture was stirred at 60° C. for 1 hour. This reaction mixture was poured in water and the resulting crystals were collected by filtration, rinsed with water, and recrystallized from ethyl acetate to provide the title compound as colorless solid (3.87 g).

Workup

  1. filtrationthe resulting crystals were collected by filtration
  2. washrinsed with water
  3. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b392a2cb266e473c9bb2f4ade1160704
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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