Ammonia → HCID 178509056, compound

HRID 2269063Notes

Reaction equation

HRID 2269063 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([SH:11])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:19])[N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:27][CH2:28][S:29][CH2:30][CH2:31][OH:32].Cl.N>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:27][CH2:28][S:29][CH2:30][CH2:31][OH:32])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:19])[N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 127372-((2-Chloroethyl)thio)ethanolHCID 1785090596-Amino-9-benzyl-8-hydroxy-2-mercaptopurine

Product 1

HCID 178509056HCID 178509056, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Crude 6-amino-9-benzyl-8-hydroxy-2-mercaptopurine (134 mg, 0.49 mmol) was suspended in dimethylformamide (50 ml). To the suspension were added potassium carbonate (100 mg, 0.73 mmol) and 2-(2-chloroethyl)thioethanol (170 mg, 1.2 mmol) in order. The mixture was stirred at room temperature for 24 hours. To the reaction mixture were added 2N hydrochloric acid and then 28% aqueous ammonia. The mixture was extracted with chloroform, the organic layer was dried on magnesium sulfate and then the solvent was removed in vacuo. The residue was purified by silica gel chromatography (5% methanol/chloroform) to give the subject compound (17 mg, yield 6%).

Workup

  1. extractionThe mixture was extracted with chloroform
  2. customthe organic layer was dried on magnesium sulfate
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified by silica gel chromatography (5% methanol/chloroform)

Sources & evidence

ORD record
ord-5425577b15ef41598535a337e6072e6f
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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