2-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)- → 2,6-dimethyl-3-(2-(4-morpholinophenyl)thiazol-5-yl)pyrimidin-4(3H)-one

HRID 56119노트

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HRID 56119 반응식
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[S:14][C:15]([NH2:18])=[CH:16][N:17]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C[Al](C)C.[NH:23](/[C:27](/[CH3:33])=[CH:28]\[C:29](OC)=[O:30])[C:24]([CH3:26])=O>C(Cl)Cl>[CH3:26][C:24]1[N:18]([C:15]2[S:14][C:13]([C:10]3[CH:9]=[CH:8][C:7]([N:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)=[CH:12][CH:11]=3)=[N:17][CH:16]=2)[C:29](=[O:30])[CH:28]=[C:27]([CH3:33])[N:23]=1

참가 물질

5

반응물 3

HCID 57053602-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)-HCID 16682925TrimethylaluminumHCID 900229082-(4-Morpholinophenyl)thiazol-5-amine

생성물 1

HCID 729485772,6-dimethyl-3-(2-(4-morpholinophenyl)thiazol-5-yl)pyrimidin-4(3H)-one수율 7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2-(4-morpholinophenyl)thiazol-5-amine (0.20 g, 0.77 mmol) in CH2Cl2 (20 mL) was added trimethylaluminum (2.3 mL, 4.6 mmol, 2 M in toluene) dropwise at rt. The reaction mixture was stirred at rt for 1 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (132 mg, 0.84 mmol) in anhydrous CH2Cl2 (5 mL). The reaction mixture was stirred at rt overnight, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (50 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by preparative TLC to give the title compound as a pale yellow solid (20 mg, 7%). The compound was characterized by the following spectroscopic data:

후처리

  1. stirringThe reaction mixture was stirred at rt overnight
  2. customquenched with saturated NH4Cl aqueous solution
  3. extractionextracted with CH2Cl2 (50 mL×3)
  4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative TLC

출처 및 근거

ORD 기록
ord-0893ecf08c374e40a862e51ea95e6d11
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434695B2

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