Pyridine → HCID 59374599, compound

HRID 888974Notes

Reaction equation

HRID 888974 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH:6]1[CH2:9][CH:8]([N:10]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])=[N:17][C:16]3[C:11]2=[N:12][C:13]([CH3:34])=[N:14][C:15]=3[N:26]2[CH2:31][CH2:30][N:29]([CH2:32][CH3:33])[CH2:28][CH2:27]2)[CH2:7]1.N1C=CC=CC=1>ClCCl>[CH3:5][O:4][C:2]([N:6]1[CH2:7][CH:8]([N:10]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])=[N:17][C:16]3[C:11]2=[N:12][C:13]([CH3:34])=[N:14][C:15]=3[N:26]2[CH2:27][CH2:28][N:29]([CH2:32][CH3:33])[CH2:30][CH2:31]2)[CH2:9]1)=[O:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 67426700HCID 67426700, compound

Product 1

HCID 59374599HCID 59374599, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add methyl chloroformate (0.0024 mol, 0.22 g, 2.5 equiv.) to a solution of 9-(azetidin-3-yl)-8-(2-chlorophenyl)-6-(4-ethylpiperazin-1-yl)-2-methyl-9H-purine (0.0009 mol, 0.4 g) and pyridine (2 mL) in dry dichloromethane (2 mL) at 0° C. and stir for 2 hours at room temperature. Quench the reaction mixture with saturated sodium bicarbonate solution and then extract with dichloromethane. Dry the organic layer over anhydrous sodium sulfate, filter and concentrate under reduced pressure to give the residue. Purify the residue by silica gel chromatography eluting with dichloromethane:methanol 98:2 to give the title compound as the freebase (0.155 g). MS (m/z): 470.63 (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 under reduced pressure
  6. customto give the residue
  7. customPurify the residue by silica gel chromatography
  8. washeluting with dichloromethane:methanol 98:2

Sources & evidence

ORD record
ord-11efa1aecdb1443f8e041a0b3777d1c3
Source dataset
uspto-grants-2012_08
Patent number
US08252798B2

Reaction notes

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