Water → HCID 57714112、化合物

HRID 1984257ノート

反応式

HRID 1984257 の反応式
[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][N:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=1)[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[N:6]=1.[CH:23]([CH:25]=[CH2:26])=[O:24].C(N(CC)CC)C.O>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][C:2]([CH3:22])([CH3:21])[CH2:3][N:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17](/[CH:26]=[CH:25]/[CH:23]=[O:24])=[CH:16][CH:15]=1)[C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]#[N:12])[N:6]=1

参加物

7

反応物 4

HCID 962WaterHCID 7847AcroleinHCID 8471TriethylamineHCID 44450361HCID 44450361、化合物

生成物 1

HCID 57714112HCID 57714112、化合物収率 50.6%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

4-[(2,2-Dimethyl-propyl)-(4-iodo-benzyl)-amino]-pyrimidine-2-carbonitrile (1.3 g, 2.5 mmoles), acrolein (0.5 ml, 7.4 mmoles), and triethylamine (0.4 ml, 3.1 mmoles) are dissolved in 25 ml of acetonitrile and Pd(OAc)2 (27 mg, 0.12 mmoles) is added at rt. The mixture is stirred at 80° C. for 18 h. Water is added and the organic layer is extracted with AcOEt, washed with brine, dried over magnesum sulfate and concentrated. The crude product is purified by silica gel column chromatography to give 423 mg of desired 4-{(2,2-dimethyl-propyl)-[4-((E)-3-oxo-propenyl)-benzyl]-amino}-pyrimidine-2-carbonitrile in 39% yield.

後処理

  1. extractionthe organic layer is extracted with AcOEt
  2. washwashed with brine
  3. dry with materialdried over magnesum sulfate
  4. concentrationconcentrated
  5. customThe crude product is purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-8ac71930e89a471c986bb77e0af8785f
出典データセット
uspto-grants-2009_06
特許番号
US07544688B2

反応ノート

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