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

HRID 1291277Notes

Reaction equation

HRID 1291277 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:19]=[CH:18][C:7]([C:8]([C:10]2[CH:17]=[CH:16][C:13]([CH2:14]Br)=[CH:12][CH:11]=2)=[O:9])=[CH:6][CH:5]=1.[SH:20][C:21]1[NH:22][C:23](=[O:30])[C:24]2[CH:29]=[CH:28][NH:27][C:25]=2[N:26]=1>CN(C=O)C>[Cl:3][C:4]1[CH:19]=[CH:18][C:7]([C:8]([C:10]2[CH:17]=[CH:16][C:13]([CH2:14][S:20][C:21]3[NH:22][C:23](=[O:30])[C:24]4[CH:29]=[CH:28][NH:27][C:25]=4[N:26]=3)=[CH:12][CH:11]=2)=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 178518762HCID 178518762, compound

Product 1

HCID 1356676022-[4-(4-Chlorobenzoyl)benzyl]thio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In DMF (20 ml) was dissolved 2-mercapto-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (836 ml) followed by addition of 1N-sodium hydroxide (5 ml). Then, under ice-cooling, a solution of 4-(4-chlorobenzoyl)benzyl bromide (1.63 g) in DMF (5 ml) was added dropwise. The mixture was stirred at room temperature for 4 hours, at the end of which time it was poured in ice-water (200 ml). The resulting precipitate was collected by filtration, rinsed with water, and dried. This precipitate was purified by flash column chromatography (3-5% ethanol-containing chloroform) to provide the title compound (1.33 g). 1H-NMR (DMSO-d6) δ: 4.52(2H,s), 6.34-6.37(1H,m), 6.91-6.95(1H,m), 7.61(2H,d,J=8.4Hz), 7.65(2H,d,J=8.4Hz), 7.70(2H,d,J=8.4Hz), 7.74(2H,d,J=8.4Hz), 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. customThis precipitate was purified by flash column chromatography (3-5% ethanol-containing chloroform)

Sources & evidence

ORD record
ord-8bfd56767a1c43879ad27eec9de92417
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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