Water → HCID 86663940, compound

HRID 2276298Notes

Reaction equation

HRID 2276298 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([N+:21]([O-:23])=[O:22])[CH:14]=2)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.[H-].[Na+].[CH3:26]I.O>CN(C)C=O>[Cl:1][C:2]1[N:10]=[C:9]([S:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([N+:21]([O-:23])=[O:22])[CH:14]=2)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178491704HCID 178491704, compound

Product 1

HCID 86663940HCID 86663940, compoundYield 741%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-chloro-2-(4-methoxy-3-nitrobenzylsulfanyl)-9H-purine (2.00 g, 6.3 mmol) was dissolved in N,N-dimethylformamide (20 ml), under ice cooling, 60% sodium hydride (0.30 g, 7.6 mmol) was added and stirred for 5 minutes, then methyl iodide (1.08 g, 0.76 mmol) was added and stirred overnight. Water was added to the reaction solution, the precipitated crystals were collected by filtration and washed sequentially with water and ether to obtain 2.06 g (89% yield) of 6-chloro-2-(4-methoxy-3-nitrobenzylsulfanyl)-9-methyl-9H-purine.

Workup

  1. stirringstirred overnight
  2. filtrationthe precipitated crystals were collected by filtration
  3. washwashed sequentially with water and ether

Sources & evidence

ORD record
ord-fbb651ab21df40ff9a47e350f7ae5ecc
Source dataset
uspto-grants-2015_09
Patent number
US09132130B2

Reaction notes

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