Nitrogen → 2,6-dimethyl-3-(6-morpholinopyridin-3-yl)pyrimidin-4(3H)-one

HRID 56151

반응식

HRID 56151 반응식
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C[Al](C)C.N#N.[NH:20](/[C:24](/[CH3:30])=[CH:25]\[C:26](OC)=[O:27])[C:21]([CH3:23])=O>C(Cl)Cl>[CH3:23][C:21]1[N:13]([C:10]2[CH:11]=[N:12][C:7]([N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[CH:8][CH:9]=2)[C:26](=[O:27])[CH:25]=[C:24]([CH3:30])[N:20]=1

참가 물질

6

반응물 4

HCID 947NitrogenHCID 1040596-(Morpholino)pyridin-3-amineHCID 57053602-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)-HCID 16682925Trimethylaluminum

생성물 1

HCID 729487572,6-dimethyl-3-(6-morpholinopyridin-3-yl)pyrimidin-4(3H)-one수율 39%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 6-morpholinopyridin-3-amine (1.79 g, 10 mmol) in CH2Cl2 (100 mL) was added trimethylaluminium (40 mL, 40 mmol, 1 M in heptane) carefully under N2. The mixture was stirred at rt for 30 min, followed by the addition of a solution of methyl 3-acetaminocrotonate (1.89 g, 12 mmol) in CH2Cl2 (5 mL). The reaction was stirred at rt for 6 h, then quenched with saturated NH4Cl aqueous solution (100 mL). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by recrystallized from EtOAc to give the title compound as a pale yellow solid (1.11 g, 39%). The compound was characterized by the following spectroscopic data:

후처리

  1. stirringThe reaction was stirred at rt for 6 h
  2. customquenched with saturated NH4Cl aqueous solution (100 mL)
  3. dry with materialThe organic phase was dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified
  6. customby recrystallized from EtOAc

출처 및 근거

ORD 기록
ord-69d5c9da52714651bccbd451dd45290a
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434695B2

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