Pyridine → HCID 58459083, compound

HRID 408820Notes

Reaction equation

HRID 408820 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]([CH2:29][C:30]([CH3:33])([OH:32])[CH3:31])[C:15]2[C:20]([N:21]=1)=[C:19]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[N:18]=[C:17]([CH3:28])[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]([CH2:29][C:30]([OH:32])([CH3:31])[CH3:33])[C:15]2[C:20]([N:21]=1)=[C:19]([N:22]1[CH2:23][CH2:24][N:25]([C:2]([O:4][CH3:5])=[O:3])[CH2:26][CH2:27]1)[N:18]=[C:17]([CH3:28])[N:16]=2

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 67434553HCID 67434553, compound

Product 1

HCID 58459083HCID 58459083, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add methyl chloroformate (0.29 g, 0.0031 mol) to a solution of 1-[8-(2-chlorophenyl)-2-methyl-6-piperazin-1-yl-purin-9-yl]-2-methyl-propan-2-ol (0.001 mol, 0.5 g) and pyridine (2.0 mL) in dry dichloromethane (3 mL) at 0° C. and stir for 2 h at room temperature. Quench the reaction mixture with saturated sodium bicarbonate solution and 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 methanol:dichloromethane (3:97) as eluent to give Methyl 4-[8-(2-chlorophenyl)-9-(2-hydroxy-2-methyl-propyl)-2-methyl-purin-6-yl]piperazine-1-carboxylate (0.3 g). ES/MS m/z 459 (M+1).

Workup

  1. customQuench the reaction mixture with saturated 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-c6fad1490f714e42a3d668c55a1eca2d
Source dataset
uspto-grants-2014_06
Patent number
US08759360B2

Reaction notes

Loading…