Water → HCID 57714145, 화합물

HRID 1984251노트

반응식

HRID 1984251 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

반응 조건

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 (3.0g, 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 wshed with AcOEt. 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 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. extractionThe organic layer is extracted with AcOEt
  4. washwashed with brine
  5. dry with materialdried over magnesum sulfate
  6. concentrationconcentrated
  7. customThe crude product is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-30821eb04cc34e05aae5cdc6ce15d3b3
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544688B2

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