Water → 6-(4-Nitrobenzylthio)-purine

HRID 900055Notes

Reaction equation

HRID 900055 reaction equation
O.[SH:2][C:3]1[N:11]=[CH:10][N:9]=[C:8]2[C:4]=1[NH:5][CH:6]=[N:7]2.O.[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1)([O-:15])=[O:14]>CN(C=O)C>[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20][S:2][C:3]2[N:11]=[CH:10][N:9]=[C:8]3[C:4]=2[NH:5][CH:6]=[N:7]3)=[CH:18][CH:17]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 962Water2×HCID 660114-Nitrobenzyl bromideHCID 178527204HCID 178527204, compound

Product 1

HCID 33195786-(4-Nitrobenzylthio)-purineYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After stirring a mixture of 30 mmol of 6-mercaptopurine monohydrate (5.12 g) and 30 mmol of water-free K2CO3 (4.12 g) in 25 mL of dry DMF for 5 minutes, 30 mmol of 4-nitrobenzylbromide (6.48 g) was added. After stirring for 4 h, 200 mL of H2O was added. The obtained solid was filtered and washed with EtOAc and CH2Cl2, followed by drying under vacuum. Yield: 91%.—White powder.

Workup

  1. stirringAfter stirring for 4 h
  2. filtrationThe obtained solid was filtered
  3. washwashed with EtOAc and CH2Cl2
  4. customby drying under vacuum

Sources & evidence

ORD record
ord-926a290d66c74628a4ed90a021b135ad
Source dataset
uspto-grants-2008_04
Patent number
US07358235B2

Reaction notes

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