Dimethylformamide → HCID 18332776, compound

HRID 2269156Notes

Reaction equation

HRID 2269156 reaction equation
[H-].[Na+].CN(C=O)C.[C:8]1([CH2:14][CH2:15][SH:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH2:17][C:18]1[N:26]=[C:25](Cl)[N:24]=[C:23]2[C:19]=1[N:20]=[CH:21][N:22]2[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>[Cl-].[Na+].O>[NH2:17][C:18]1[N:26]=[C:25]([S:16][CH2:15][CH2:14][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:24]=[C:23]2[C:19]=1[N:20]=[CH:21][N:22]2[CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 781262-PhenylethanethiolHCID 2764829-Benzyl-2-chloro-9h-purin-6-amine

Product 1

HCID 18332776HCID 18332776, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

Sodium hydride (300 mg, 7.5 mmol 60% in mineral oil) were added DMF (10 ml), 2-phenylethanethiol (1 ml, 7 mmol) and 6-amino-9-benzyl-2-chloropurine (100 mg, 0.39 mmol) in order. The mixture was stirred at 100° C. for 10 hours. After addition of saturated brine the mixture was extracted with ethyl acetate. The organic layer was dried on magnesium sulfate and the solvent was removed in vacuo. The residue was purified with silica gel chromatography (1% methanol/chloroform) to give the subject compound (51 mg, yield 37%).

Workup

  1. extractionwas extracted with ethyl acetate
  2. customThe organic layer was dried on magnesium sulfate
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified with silica gel chromatography (1% methanol/chloroform)

Sources & evidence

ORD record
ord-efe4180b6b6547549ce8a9c358e4dfda
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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