4-(6-Chloronicotinoyl)benzyl bromide → 2-[4-(6-Chloronicotinoyl)benzylthio]-3-methylthieno[3,2-d]pyrimidin-4(3H)-one

HRID 1291347Notes

Reaction equation

HRID 1291347 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.[Cl:16][C:17]1[CH:32]=[CH:31][C:20]([C:21]([C:23]2[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=2)=[O:22])=[CH:19][N:18]=1>C(O)C.O>[Cl:16][C:17]1[CH:32]=[CH:31][C:20]([C:21]([C:23]2[CH:30]=[CH:29][C:26]([CH2:27][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:25][CH:24]=2)=[O:22])=[CH:19][N:18]=1

Participants

6

Reactant 3

HCID 189188004-(6-Chloronicotinoyl)benzyl bromideHCID 23719242Sodium hydroxide--water (1/1/1)HCID 178481668HCID 178481668, compound

Product 1

HCID 189187982-[4-(6-Chloronicotinoyl)benzylthio]-3-methylthieno[3,2-d]pyrimidin-4(3H)-oneYield 74.7%

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 (10.5 ml) in ethanol (30 ml) was added 4-(6-chloronicotinoyl)benzyl bromide (3.35 g) and the mixture was stirred at 60° C. fro 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 light-yellow solid (3.194 g).

Workup

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

Sources & evidence

ORD record
ord-df96414ab3f6453bbb652154ff97026a
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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