Sodium Hydroxide → HCID 135667586, compound

HRID 1291280Notes

Reaction equation

HRID 1291280 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:23]=[C:24]([CH:27]=[CH:28][CH:29]=2)[CH2:25]Br)=[O:21])=[CH:18][CH:17]=1>CO.COCCOC.CN(C=O)C>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([C:22]2[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=2)[CH2:25][S:12][C:7]2[NH:8][C:9](=[O:11])[C:10]3[C:2]([CH3:1])=[CH:3][NH:4][C:5]=3[N:6]=2)=[O:21])=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 136496533-(4-Chlorobenzoyl)benzyl bromideHCID 178430835HCID 178430835, compound

Product 1

HCID 135667586HCID 135667586, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 18463208dimethoxyethane N,N-dimethylformamideSolvent

Procedure

In methanol (18.7 ml) was suspended 5-methyl-2-mercapto-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (1.36 g) followed by addition of 1N-sodium hydroxide (7.88 ml) for dissolution. Then, under ice-cooling, a solution of 3-(4-chlorobenzoyl)benzyl bromide (2.79 g) in DME-DMF (6:5; 22 ml) was added dropwise. The mixture was stirred at room temperature for 20 hours, at the end of which time it was poured in ice-water (200ml). The resulting precipitate was collected by filtration and rinsed with water. Then, it was further washed with 50% ethanol/water, methanol and ether in that order, dried, and purified by flash column chromatography (chloroform, containing 1% methanol) to provide the title compound (1.94 g). 1H-NMR (DMSO-d6) δ: 2.25(3H,s), 4.50(2H,s), 6.65(1H,s), 7.50(2H,d,J=8.OHz), 7.69(2H,d,J=8.6Hz), 7.51-7.82(4H,m), 11.38(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. washThen, it was further washed with 50% ethanol/water, methanol and ether in that order
  5. customdried
  6. custompurified by flash column chromatography (chloroform, containing 1% methanol)

Sources & evidence

ORD record
ord-fc33f09dcb254ddc94af59cb3e531b8d
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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