Water → HCID 57714112, 화합물

HRID 1984257노트

반응식

HRID 1984257 반응식
[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

참가 물질

7

반응물 4

HCID 962WaterHCID 7847AcroleinHCID 8471TriethylamineHCID 44450361HCID 44450361, 화합물

생성물 1

HCID 57714112HCID 57714112, 화합물수율 50.6%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8ac71930e89a471c986bb77e0af8785f
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544688B2

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