9-Benzyl-2-chloro-9h-purin-6-amine → HCID 18332754, compound

HRID 2269084Notes

Reaction equation

HRID 2269084 reaction equation
[NH2:1][C:2]1[N:10]=[C:9](Cl)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:19]1([S-:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Na+]>CN(C=O)C.[Cl-].[Na+].O>[NH2:1][C:2]1[N:10]=[C:9]([S:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 2764829-Benzyl-2-chloro-9h-purin-6-amineHCID 4110039Sodium benzenethiolate

Product 1

HCID 18332754HCID 18332754, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

6-Amino-9-benzyl-2-chloropurine (200 mg, 0.77 mmol) and sodium thiophenolate (2 g, 15 mmol) were mixed in DMF (12 ml) and then the mixture was stirred under heating at 100° C. for 7.5 hours. To the reaction mixture was added brine and the mixture was extracted with ethyl acetate. The organic layer was dried on magnesium sulfate, filtered and the solvent in the filtrate was evaporated in vacuo. The residue was purified with silica gel chromatography (0.5% methanol/chloroform) to give the subject compound (228 mg, yield 89%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was dried on magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent in the filtrate was evaporated in vacuo
  5. customThe residue was purified with silica gel chromatography (0.5% methanol/chloroform)

Sources & evidence

ORD record
ord-e21916d7a2f54eff8689f4497cce8bd7
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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