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

HRID 501105Notes

Reaction equation

HRID 501105 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:20]([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)=[N:21][CH:22]=[CH:23][CH:24]=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[CH:24]=[CH:23][CH:22]=[N:21][C:20]=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'-CarbonyldiimidazoleHCID 22293209tert-Butyl 4-[({3-[(2,4-dimethoxybenzyl)amino]pyridin-2-yl}methyl)amino]piperidine-1-carboxylate

Product 1

HCID 22293253tert-Butyl 4-[1-(2,4-dimethoxybenzyl)-2-oxo-1,4-dihydropyrido[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

Carbonyldiimidazole (1.22 g, 7.53 mmol) was added to a solution of the material from Step C in dimethylformamide (20 mL) and the reaction was heated to 150° C. overnight. 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, 30 to 100% ethyl acetate in methylene chloride gradient elution), which gave the title compound (0.10 g). MS 483.3 (M+1).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialthe organic phase dried over sodium sulfate
  3. customThe crude product was purified by chromatography (silica gel, 30 to 100% ethyl acetate in methylene chloride gradient elution), which

Sources & evidence

ORD record
ord-f8910f9f649d496d9a1f3022c8f76591
Source dataset
uspto-grants-2010_08
Patent number
US07772224B2

Reaction notes

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