3,3-Dimethylglutaric anhydride → 1-(5-Methoxy-pyrimidin-2-yl)-4,4-dimethyl-piperidine-2,6-dione

HRID 1831054Notes

Reaction equation

HRID 1831054 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]([NH2:9])=[N:7][CH:8]=1.[CH3:10][C:11]1([CH3:19])[CH2:17][C:16](=O)[O:15][C:13](=[O:14])[CH2:12]1>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]([N:9]2[C:13](=[O:14])[CH2:12][C:11]([CH3:19])([CH3:10])[CH2:17][C:16]2=[O:15])=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 778133,3-Dimethylglutaric anhydrideHCID 23052442-Amino-5-methoxypyrimidine

Product 1

HCID 220478711-(5-Methoxy-pyrimidin-2-yl)-4,4-dimethyl-piperidine-2,6-dioneYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 5-methoxy-pyrimidin-2-ylamine (1.00 g, 7.99 mmol) and 3,3-dimethylglutaric anhydride (1.14 g, 7.99 mmol) was heated at 180° C. for 9 hours. After cooling to room temperature the reaction mixture was dissolved in a small amount of dichloromethane and purified by flash column chromatography (SiO2, ethyl acetate:heptane 70:30), yielding the title compound (0.79 g, 40% yield) as a white solid.

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. custompurified by flash column chromatography (SiO2, ethyl acetate:heptane 70:30)

Sources & evidence

ORD record
ord-bc7cd82206f348c6912166b51957f868
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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