Dimethylformamide → HCID 18332809, compound

HRID 2269155Notes

Reaction equation

HRID 2269155 reaction equation
[H-].[Na+].CN(C=O)C.[SH:8][CH2:9][CH2:10][CH2:11][OH:12].[NH2:13][C:14]1[N:22]=[C:21](Cl)[N:20]=[C:19]2[C:15]=1[N:16]=[CH:17][N:18]2[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>[Cl-].[Na+].O>[NH2:13][C:14]1[N:22]=[C:21]([S:8][CH2:9][CH2:10][CH2:11][OH:12])[N:20]=[C:19]2[C:15]=1[N:16]=[CH:17][N:18]2[CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 882113-MercaptopropanolHCID 2764829-Benzyl-2-chloro-9h-purin-6-amine

Product 1

HCID 18332809HCID 18332809, compoundYield 12.4%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

Sodium hydride (600 mg, 15 mmol 60% in mineral oil) were added DMF (10 ml), 3-mercapto-1-propanol (1 ml, 12 mmol) and 6-amino-9-benzyl-2-chloropurine (200 mg, 0.77 mmol) in order. The mixture was stirred at 100° C. for 2 hours. After addition of saturated brine the reaction 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 (30 mg, yield 12%).

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-1bf826ce837745f994717a6f7bcbc2ba
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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