Water → HCID 57714145、化合物

HRID 1163026ノート

反応式

HRID 1163026 の反応式
[O:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[Li]CCCC.[CH3:11][C:12]([CH3:32])([CH3:31])[CH2:13][N:14]([CH2:23][C:24]1[CH:29]=[CH:28][C:27](I)=[CH:26][CH:25]=1)[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([C:21]#[N:22])[N:16]=1.O>C1COCC1.[Cl-].[Cl-].[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:11][C:12]([CH3:32])([CH3:31])[CH2:13][N:14]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[O:1][CH:5]=[CH:4][N:3]=2)=[CH:26][CH:25]=1)[C:15]1[CH:20]=[CH:19][N:18]=[C:17]([C:21]#[N:22])[N:16]=1

参加物

8

反応物 4

HCID 962WaterHCID 9255OxazoleHCID 44450361HCID 44450361、化合物HCID 178418339Butyllithium

生成物 1

HCID 57714145HCID 57714145、化合物収率 16%

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of oxazole (0.5 ml, 7.2 mmoles) in 10 ml of THF at −78° C. is added BuLi (5.23 ml, 8.0 mmoles, 1.6 M solution in hexane). After 30 min, ZnCl2 (3.0 g, 21.7 mmoles) and then a solution of 4-{(2,2-Dimethyl-propyl)-[4-iodo-benzyl]-amino}-pyrimidine-2-carbonitrile (2.9 g, 7.2 mmoles) in 10 ml of THF are added. The reaction mixture is warmed to 0° C. for 1 h. The reaction mixture is added to Pd(PPh3)4 (0.9 g, 0.8 mmoles) and heated to reflux. Water is added and is filtered through a pad of Celite which is washed with AcOEt. The organic layer is extracted with AcOEt, washed with brine, dried over magnesium sulfate and concentrated. The crude product is purified by silica gel column chromatography to give 104 mg of desired 4-[(2,2-dimethyl-propyl)-(4-oxazol-2-yl-benzyl)-amino]-pyrimidine-2-carbonitrile in 16% yield.

後処理

  1. temperatureheated to reflux
  2. filtrationis filtered through a pad of Celite which
  3. washis washed with AcOEt
  4. extractionThe organic layer is extracted with AcOEt
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe crude product is purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-348215da67364b8980a862494ef558b2
出典データセット
uspto-grants-2010_10
特許番号
US07820818B2

反応ノート

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