Sodium Hydroxide → 2-[4-(4-Fluorobenzoyl)benzyl]thio-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

HRID 1291278Notes

Reaction equation

HRID 1291278 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7]([SH:12])=[N:6][C:5]=2[NH:4][CH:3]=1.[OH-].[Na+].[F:15][C:16]1[CH:31]=[CH:30][C:19]([C:20]([C:22]2[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=2)=[O:21])=[CH:18][CH:17]=1>CO.COCCOC>[F:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([C:22]2[CH:29]=[CH:28][C:25]([CH2:26][S:12][C:7]3[NH:8][C:9](=[O:11])[C:10]4[C:2]([CH3:1])=[CH:3][NH:4][C:5]=4[N:6]=3)=[CH:24][CH:23]=2)=[O:21])=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 47290134-(4-Fluorobenzoyl)benzyl bromideHCID 178430835HCID 178430835, compound

Product 1

HCID 1356675982-[4-(4-Fluorobenzoyl)benzyl]thio-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-oneYield 68.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

In methanol (25 ml) was suspended 5-methyl-2-mercapto-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (1.82 g) followed by addition of 1N-sodium hydroxide (10.5 ml) for dissolution. Then, under ice-cooling, a solution of 4-(4-fluorobenzoyl)benzyl bromide (3.51 g) in DME (10 ml) was added dropwise. The mixture was stirred at room temperature for 4 hours and the resulting crystalline precipitate was collected by filtration and rinsed with water. The crystals were further rinsed with 50% ethanol/water, methanol and ether serially, dried, and recrystallized from DME (1,2-dimethoxyethane) to provide the title compound (2.71 g). 1H-NMR (DMSO-d6) δ: 2.24(3H,s), 4.51(2H,s), 6.65(1H,s), 7.37(2H,t,J=8.8Hz), 7.64(2H,d,J=8.8Hz), 7.70(2H,d,J=8.8Hz), 7.81(2H,dd,J=5.6,8.8Hz), 11.43(1H,s), 11.97(1H,s).

Workup

  1. temperatureThen, under ice-cooling
  2. filtrationthe resulting crystalline precipitate was collected by filtration
  3. washrinsed with water
  4. washThe crystals were further rinsed with 50% ethanol/water, methanol and ether serially
  5. customdried
  6. customrecrystallized from DME (1,2-dimethoxyethane)

Sources & evidence

ORD record
ord-3b0a5de463514b8da4cc91a11185e343
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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