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

HRID 633977Notes

Reaction equation

HRID 633977 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-45840ed07c4f4489b3b53763010e5a61
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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