2-Chloro-N,N-dimethylethylamine → HCID 178483977, compound

HRID 2269038Notes

Reaction equation

HRID 2269038 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+].[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29]Cl>CN(C)C=O>[NH2:1][C:2]1[N:10]=[C:9]([S:11][CH2:29][CH2:28][N:27]([CH3:31])[CH3:26])[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

5

Reactant 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 11430Potassium CarbonateHCID 1785090596-Amino-9-benzyl-8-hydroxy-2-mercaptopurine

Product 1

HCID 178483977HCID 178483977, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Crude 6-amino-9-benzyl-8-hydroxy-2-mercaptopurine (200 mg, 0.73 mmol) was suspended in dimethylformamide (80 ml). To the suspension were added potassium carbonate (300 mg, 2.2 mmol) and 2-dimethylaminoethylchloride (160 mg, 1.1 mmol) in order. The mixture was stirred at room temperature for 11 hours. The solvent was removed in vacuo, and the residue was purified by silica gel chromatography (10% methanol/chloroform) to give the subject compound (9 mg, yield 4%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography (10% methanol/chloroform)

Sources & evidence

ORD record
ord-5c0f2af0cd7d4493a283d9200676f4e4
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

Loading…