Dimethylformamide → HCID 18332687, compound

HRID 2269083Notes

Reaction equation

HRID 2269083 reaction equation
CN(C=O)C.[H-].[Na+].[CH:8]1([SH:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[NH2:15][C:16]1[N:24]=[C:23](Cl)[N:22]=[C:21]2[C:17]=1[N:18]=[CH:19][N:20]2[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>[Cl-].[Na+].O>[NH2:15][C:16]1[N:24]=[C:23]([S:14][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[N:22]=[C:21]2[C:17]=1[N:18]=[CH:19][N:20]2[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 15290CyclohexanethiolHCID 24758Sodium hydrideHCID 2764829-Benzyl-2-chloro-9h-purin-6-amine

Product 1

HCID 18332687HCID 18332687, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

To DMF suspension (10 ml) containing sodium hydride (256 mg, 6.4 mmol, 60% in mineral oil) were added cyclohexanethiol (2 ml, 16 mmol) and 6-amino-9-benzyl-2-chloropurine (100 mg, 0.39 mmol) in order. The mixture was heated at 100° C. for 3.5 hours. Brine was added thereto and the mixture was extracted with ethyl acetate. 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 (1% methanol/chloroform) to give the subject compound (112 mg, yield 86%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  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 (1% methanol/chloroform)

Sources & evidence

ORD record
ord-8557eae6c807413d95ef90b24bee22cd
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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