Water → HCID 57714145, 화합물

HRID 1163026노트

반응식

HRID 1163026 반응식
[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

참가 물질

8

반응물 4

HCID 962WaterHCID 9255OxazoleHCID 44450361HCID 44450361, 화합물HCID 178418339Butyllithium

생성물 1

HCID 57714145HCID 57714145, 화합물수율 16%

시약·촉매·용매 3

HCID 3007855Zincchloride촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-348215da67364b8980a862494ef558b2
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820818B2

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