Pyridine → HCID 62705988, compound

HRID 2370074Notes

Reaction equation

HRID 2370074 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[N:14]([CH2:30][CH2:31][NH2:32])[C:15]2[C:20]([N:21]=1)=[C:19]([N:22]1[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]1)[N:18]=[C:17]([CH3:29])[N:16]=2.N1C=CC=CC=1>ClCCl>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[N:14]([CH2:30][CH2:31][NH:32][C:2](=[O:3])[O:4][CH3:5])[C:15]2[C:20]([N:21]=1)=[C:19]([N:22]1[CH2:23][CH2:24][N:25]([CH3:28])[CH2:26][CH2:27]1)[N:18]=[C:17]([CH3:29])[N:16]=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 67449594HCID 67449594, compound

Product 1

HCID 62705988HCID 62705988, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add methyl chloroformate (0.25 g, 0.0027 mol) to a solution of 2-[8-(2-chlorophenyl)-2-methyl-6-(4-methylpiperazin-1-yl)purin-9-yl]ethanamine (0.39 g, 0.0010 mol) and pyridine (4.0 mL) in dry dichloromethane (4 mL) at 0° C. Allow to warm to room temperature and stir for 2 hour. Quench the reaction mixture with saturated aqueous sodium bicarbonate solution and then extract with dichloromethane. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate to give a residue. Purify the residue on a silica gel column using dichloromethane:methanol (97:3) as eluent to afford methyl N-[2-[8-(2-chlorophenyl)-2-methyl-6-(4-methylpiperazin-1-yl)purin-9-yl]ethyl]carbamate (0.3 g). ES/MS m/z 444 (M+1).

Workup

  1. customQuench the reaction mixture with saturated aqueous sodium bicarbonate solution
  2. extractionextract with dichloromethane
  3. dry with materialDry the organic layer over anhydrous sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customto give a residue
  7. customPurify the residue on a silica gel column

Sources & evidence

ORD record
ord-dae6bb5c996c409e8b933e8e2e972922
Source dataset
uspto-grants-2014_04
Patent number
US08710063B2

Reaction notes

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