Reaction #42044

ord-36135d3303a04a40b4b6210a71dba260

Reaction equation

COC(OC)N(C)C
N,N-dimethylformamide dimethylacetal
CC(=O)c1cncnc1
5-acetylpyrimidine
CC(C)OC(C)C
diisopropyl ether
CN(C)C=CC(=O)c1cncnc1
objective compound
Yield 68.0%
CN(C)C=CC(=O)c1cncnc1
3-(dimethylamino)-1-(5-pyrimidinyl)-2-propen-1-one
Yield 68.0%

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturethe mixture was heated
  2. 2
    Temperatureat reflux for 15 hours
  3. 3
    TemperatureAfter the reaction solution was air-cooled
  4. 4
    Filtrationthe deposited crystal was collected by filtration

Procedure

6.01 g of N,N-dimethylformamide dimethylacetal was added to 1.54 g of 5-acetylpyrimidine (Khim. Geterotsikl. Soedim., 1981, (7), 958-962) and the mixture was heated at reflux for 15 hours. After the reaction solution was air-cooled, a small amount of diisopropyl ether was added and the deposited crystal was collected by filtration to obtain 1.52 g of the objective compound as reddish brown crystals.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07728131B2uspto-grants-2010_06