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N,N-Dimethylaniline → 4-Chloro-3-(2-chloroethyl)-8-mesityl-2,6-dimethylimidazo[1,5-a]pyrimidine

HRID 584803
ノート
印刷プレビュー

反応式

HRID 584803 の反応式
[Cl:1][CH2:2][CH2:3][C:4]1[C:5]([CH3:24])=[N:6][C:7]2[N:8]([C:11]([CH3:23])=[N:12][C:13]=2[C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=2[CH3:22])[C:9]=1O.CN(C)C1C=CC=CC=1.NC(CC)CC.O.P(Cl)(Cl)([Cl:43])=O>C(#N)C>[Cl:43][C:9]1[N:8]2[C:11]([CH3:23])=[N:12][C:13]([C:14]3[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[CH3:22])=[C:7]2[N:6]=[C:5]([CH3:24])[C:4]=1[CH2:3][CH2:2][Cl:1]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 949N,N-DimethylanilineHCID 962WaterHCID 120193-PentanamineHCID 24813Phosphorus oxychlorideHCID 178424660HCID 178424660、化合物

生成物 1

HCID 222495154-Chloro-3-(2-chloroethyl)-8-mesityl-2,6-dimethylimidazo[1,5-a]pyrimidine

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

反応条件

温度
80 °C

実験手順

A solution of 3-(2-chloroethyl)-8-mesityl-2,6-dimethylimidazo[1,5-a]pyrimidin-4-ol (200 mg, 0.58 mmol) and N,N-dimethylaniline (0.3 mL) in phosphorus oxychloride (3 mL) was heated under reflux for six hours. After overnight, 3-aminopentane (2 mL) was added to a solution of the residue in acetonitrile (5 mL), followed by stirring at 80° C. for three hours. Water was added, and the mixture was extracted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatogrpahy (10-20% ethyl acetate/hexane), to give the title compound (139 mg) as pale yellow crystals.

後処理

  1. temperatureunder reflux for six hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatogrpahy (10-20% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-4bec78097ef2461aa28f0c8fb141cbd6
出典データセット
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06927221B2

反応ノート

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