Nitrogen → 3-(4-(1,1-dioxidothiomorpholino)-3-fluorophenyl)-2,6-dimethyl pyrimidin-4(3H)-one

HRID 56099노트

반응식

HRID 56099 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][S:11](=[O:15])(=[O:14])[CH2:10][CH2:9]2)=[C:4]([F:16])[CH:3]=1.C[Al](C)C.N#N.[NH:23](/[C:27](/[CH3:33])=[CH:28]\[C:29](OC)=[O:30])[C:24]([CH3:26])=O>C(Cl)Cl>[O:15]=[S:11]1(=[O:14])[CH2:12][CH2:13][N:8]([C:5]2[CH:6]=[CH:7][C:2]([N:1]3[C:29](=[O:30])[CH:28]=[C:27]([CH3:33])[N:23]=[C:24]3[CH3:26])=[CH:3][C:4]=2[F:16])[CH2:9][CH2:10]1

참가 물질

6

반응물 4

HCID 947NitrogenHCID 57053602-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)-HCID 16682925TrimethylaluminumHCID 435813994-(4-Amino-2-fluorophenyl)thiomorpholine 1,1-dioxide

생성물 1

HCID 729482083-(4-(1,1-dioxidothiomorpholino)-3-fluorophenyl)-2,6-dimethyl pyrimidin-4(3H)-one수율 47%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 4-(4-amino-2-fluorophenyl)1,1-dioxidothiomorpholine (1.20 g, 4.91 mmol) in anhydrous CH2Cl2 (100 mL) was added trimethylaluminium (28.5 mL, 28.5 mmol, 1 M in heptane) carefully dropwise under N2. Upon the end of addition the mixture was stirred at rt for 20 min, followed by the addition of a solution of methyl 3-acetaminocrotonate (2.32 g, 14.76 mmol) in anhydrous CH2Cl2 (30 mL). Upon the end of addition the reaction mixture was stirred at rt for another 15 h, then quenched with an appropriate amount of water and extracted with CH2Cl2. The combined organic phases were washed with brine, dried and concentrated in vacuo to give the title compound as a yellow solid (0.81 g, 47%). The compound was characterized by the following spectroscopic data:

후처리

  1. additionUpon the end of addition the mixture
  2. additionUpon the end of addition the reaction mixture
  3. stirringwas stirred at rt for another 15 h
  4. customquenched with an appropriate amount of water
  5. extractionextracted with CH2Cl2
  6. washThe combined organic phases were washed with brine
  7. customdried
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e05d37329d0140c7bd8c4f064bc5958b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434695B2

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