1,1'-Carbonyldiimidazole → tert-Butyl 4-(1-(2,4-dimethoxybenzyl)-1,2-dihydro-2-oxopyrido[2,3-d]pyrimidin-3(4H)-yl)piperidine-1-carboxylate

HRID 493613

Reaction equation

HRID 493613 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH3:13][O:14][C:15]1[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[CH:40][C:16]=1[CH2:17][NH:18][C:19]1[C:24]([CH2:25][NH:26][CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]2)=[CH:23][CH:22]=[CH:21][N:20]=1>CN(C)C=O.O>[CH3:13][O:14][C:15]1[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[CH:40][C:16]=1[CH2:17][N:18]1[C:19]2[N:20]=[CH:21][CH:22]=[CH:23][C:24]=2[CH2:25][N:26]([CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]2)[C:1]1=[O:2]

Participants

5

Reactant 2

HCID 682631,1'-Carbonyldiimidazole2×HCID 22293293Tert-butyl 4-((2-(2,4-dimethoxybenzylamino)pyridin-3-yl)methylamino)piperidine-1-carboxylate

Product 1

HCID 22293273tert-Butyl 4-(1-(2,4-dimethoxybenzyl)-1,2-dihydro-2-oxopyrido[2,3-d]pyrimidin-3(4H)-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

Carbonyldiimidazole (0.65 g, 4.0 mmol) was added to a solution of the material from Step C in dimethylformamide (20 mL) and the reaction was heated to 150° C. After 1 d, further carbonyldiimidazole (0.65 g, 4.0 mmol) was added and the reaction heated for an additional 3 h. The reaction was diluted with water and extracted with dichloromethane, and the organic phase dried over sodium sulfate. The crude product was purified by chromatography (silica gel, 20 to 80% ethyl acetate in methylene chloride gradient elution), which gave the title compound (0.35 g). MS 483.3 (M+1).

Workup

  1. temperaturethe reaction heated for an additional 3 h
  2. extractionextracted with dichloromethane
  3. dry with materialthe organic phase dried over sodium sulfate
  4. customThe crude product was purified by chromatography (silica gel, 20 to 80% ethyl acetate in methylene chloride gradient elution), which

Sources & evidence

ORD record
ord-fb92df9cd9c042228f571e8b1f904b40
Source dataset
uspto-grants-2009_05
Patent number
US07534784B2

Linked notes

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