Dabco → Methyl-phenyl-carbamic Acid 2-(4,4-dimethyl-2,6-dioxo-piperidin-1-yl)-pyrimidin-5-yl Ester

HRID 1831309Notes

Reaction equation

HRID 1831309 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[C:13](=[O:14])[CH2:12][C:11]([CH3:16])([CH3:15])[CH2:10][C:9]2=[O:17])=[N:6][CH:7]=1.[CH3:18][N:19]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:20](Cl)=[O:21].N12CCN(CC1)CC2>ClCCl>[CH3:16][C:11]1([CH3:15])[CH2:10][C:9](=[O:17])[N:8]([C:5]2[N:6]=[CH:7][C:2]([O:1][C:20](=[O:21])[N:19]([CH3:18])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:3][N:4]=2)[C:13](=[O:14])[CH2:12]1

Participants

5

Reactant 3

HCID 9237DabcoHCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 220477581-(5-Hydroxy-pyrimidin-2-yl)-4,4-dimethyl-piperidine-2,6-dione

Product 1

HCID 69518140Methyl-phenyl-carbamic Acid 2-(4,4-dimethyl-2,6-dioxo-piperidin-1-yl)-pyrimidin-5-yl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(5-hydroxy-pyrimidin-2-yl)-4,4-dimethyl-piperidine-2,6-dione (0.60 g, 2.55 mmol), N-methyl-N-phenylcarbamoyl chloride (0.48 g, 2.81 mmol) and 1,4-diazabicyclo-[2,2,2]octane (0.31 g, 2.81 mmol) in dichloromethane (25 mL) was stirred at room temperature for 15 minutes. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 50:50), yielding the title compound as a white solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane 50:50)

Sources & evidence

ORD record
ord-2bf1cdb7f6c345788428e046bda42733
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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