Dimethylformamide → HCID 18332726, compound

HRID 2269086Notes

Reaction equation

HRID 2269086 reaction equation
CN(C=O)C.[H-].[Na+].[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[SH:18].[NH2:19][C:20]1[N:28]=[C:27](Cl)[N:26]=[C:25]2[C:21]=1[N:22]=[CH:23][N:24]2[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>[Cl-].[Na+].O>[NH2:19][C:20]1[N:28]=[C:27]([S:18][C:9]2[CH:10]=[CH:11][C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:8]=2)[N:26]=[C:25]2[C:21]=1[N:22]=[CH:23][N:24]2[CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 70582-NaphthalenethiolHCID 24758Sodium hydrideHCID 2764829-Benzyl-2-chloro-9h-purin-6-amine

Product 1

HCID 18332726HCID 18332726, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

To DMF suspension (20 ml) containing sodium hydride (800 mg, 20 mmol, 60% in mineral oil) were added 2-naphthalenethiol (3.8 g, 24 mmol) and 6-amino-9-benzyl-2-chloropurine (200 mg, 0.77 mmol) in order. The mixture was stirred under heating at 100° C. for 10.5 hours. Brine was added thereto and the mixture was extracted with chloroform. The organic layer was dried on magnesium sulfate, filtrated 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 (244 mg, yield 83%).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. customThe organic layer was dried on magnesium sulfate
  3. filtrationfiltrated
  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-53ca4cfa0c0a44619ed22f4f58b6cbb8
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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