1,1'-Carbonyldiimidazole → 6-Bromo-3-(2-(4-methylpiperazin-1-yl)ethyl)-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-one

HRID 2172078Notes

Reaction equation

HRID 2172078 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[Br:13][C:14]1[CH:15]=[C:16]([CH2:21][NH:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]2)[C:17]([NH2:20])=[N:18][CH:19]=1>O1CCOCC1>[Br:13][C:14]1[CH:19]=[N:18][C:17]2[NH:20][C:6](=[O:7])[N:22]([CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]3)[CH2:21][C:16]=2[CH:15]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 671545225-Bromo-3-((2-(4-methylpiperazin-1-yl)ethylamino)methyl)pyridin-2-amine

Product 1

HCID 671546046-Bromo-3-(2-(4-methylpiperazin-1-yl)ethyl)-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

CDI (815 mg, 5.0 mmol) was added to a solution of 5-bromo-3-((2-(4-methylpiperazin-1-yl)ethylamino)methyl)pyridin-2-amine (550 mg, 1.67 mmol) in dioxane (13 mL). The reaction mixture was stirred overnight at reflux. After concentration to dryness, the residue was purified by chromatography on silica gel using dichloromethane/methanol/ammoniac (10:0:0.1 to 9:1:0.1) as eluent. The title product was obtained as a yellow solid (430 mg, 72%).

Workup

  1. temperatureat reflux
  2. concentrationAfter concentration to dryness
  3. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-21eb8d92bdcb4a3594239a7cc1528a3c
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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