Diisopropyl Ether → 1-(5-Pyrimidyl)-3-(dimethylamino)-2-propene-1-one

HRID 13766Notes

Reaction equation

HRID 13766 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[C:9]([C:12]1[CH:13]=[N:14][CH:15]=[N:16][CH:17]=1)(=[O:11])[CH3:10].C(OC(C)C)(C)C>>[CH3:6][N:4]([CH3:5])[CH:3]=[CH:10][C:9]([C:12]1[CH:13]=[N:14][CH:15]=[N:16][CH:17]=1)=[O:11]

Participants

4

Reactant 3

HCID 7914Diisopropyl EtherHCID 78373Dimethylformamide dimethyl acetalHCID 5723081-(5-Pyrimidinyl)ethanone

Product 1

HCID 534210051-(5-Pyrimidyl)-3-(dimethylamino)-2-propene-1-oneYield 68%

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.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 15 hours
  3. temperatureAfter the reaction solution was air-cooled
  4. filtrationthe deposited crystal was collected by filtration

Sources & evidence

ORD record
ord-36135d3303a04a40b4b6210a71dba260
Source dataset
uspto-grants-2010_06
Patent number
US07728131B2

Reaction notes

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