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

HRID 1291276Notes

Reaction equation

HRID 1291276 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+].[Cl: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>CN(C)C=O>[Cl: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

5

Reactant 3

HCID 14798Sodium HydroxideHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 178430835HCID 178430835, compound

Product 1

HCID 1356676042-[4-(4-Chlorobenzoyl)benzyl]thio-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-oneYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In dimethylformamide (30 ml) was dissolved 5-methyl-2-mercapto-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (1.36 g) followed by addition of 1N-sodium hydroxide (7.5 ml). Then, under ice-cooling, a solution of 4-(4-chlorobenzoyl)benzyl bromide (2.48 g) in DMF (10 ml) was added dropwise. The mixture was then stirred at room temperature for 4 hours, at the end of which time it was poured in ice-water (250 ml). The resulting precipitate was collected by filtration, rinsed with water, and dried. The dried precipitate was purified by flash column chromatography (3-5% ethanol-containing chloroform) to provide the title compound (1.57 g). IH-NMR (DMSO-d6) 6: 2.23(3H,s), 4.50(2H,s), 6.65(1H,s), 7.60(2H,d,J=8.6Hz), 7.64(2H,d,J=8.6Hz), 7.69(2H,d,J=8.6Hz), 7.74(2H,d,J=8.6Hz), 11.42(1H,s), 11.95(1H,s).

Workup

  1. temperatureThen, under ice-cooling
  2. filtrationThe resulting precipitate was collected by filtration
  3. washrinsed with water
  4. customdried
  5. customThe dried precipitate was purified by flash column chromatography (3-5% ethanol-containing chloroform)

Sources & evidence

ORD record
ord-e0d72c1a340d463eb190e1f240008816
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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