Sodium hydride → Methyl 4-(4-fluorophenyl)-6-(1-methylethyl)-2-(methyl(methylsulfonyl)amino)-5-pyrimidinecarboxylate

HRID 50106노트

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HRID 50106 반응식
[NH2:1][C:2](=[C:10]([C:15](=O)[CH:16]([CH3:18])[CH3:17])[C:11]([O:13][CH3:14])=[O:12])[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.CN(C)C(=O)C.[C:26]([N:28]([CH3:33])[S:29]([CH3:32])(=[O:31])=[O:30])#[N:27].[H-].[Na+]>O>[F:9][C:6]1[CH:7]=[CH:8][C:3]([C:2]2[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:15]([CH:16]([CH3:18])[CH3:17])[N:27]=[C:26]([N:28]([S:29]([CH3:32])(=[O:31])=[O:30])[CH3:33])[N:1]=2)=[CH:4][CH:5]=1

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 10219456N-cyano-N-methylmethanesulphonamideHCID 178500902HCID 178500902, 화합물

생성물 1

HCID 9929821Methyl 4-(4-fluorophenyl)-6-(1-methylethyl)-2-(methyl(methylsulfonyl)amino)-5-pyrimidinecarboxylate수율 29.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

2.66 g (10.0 mmol) of methyl 2-[1-amino-1-(4-fluorophenyl)methylene]-4-methyl-3-oxopentanoate were introduced into 12 g of N,N-dimethylacetamide together with 2.70 g (20.0 mmol) of N-cyano-N-methylmethanesulphonamide. 440 mg (11.0 mmol) of sodium hydride (60% in oil) were added to this solution at room temperature over the course of 2 h. An orange-red clear solution was obtained. After 6 h at room temperature, the reaction solution was poured onto 25 ml of water. The suspension was stirred in an ice bath for 30 minutes, and the precipitate was filtered off and washed with water (2×10 ml). After drying in a high vacuum, 1.11 g (29.1%) of methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulphonyl-N-methylamino)pyrimidine-5-carboxylate were obtained in the form of a pale beige solid. The product still contained traces of methyl 2-[1-amino-1-(4-fluorophenyl)methylene]-4-methyl-3-oxopentanoate.

후처리

  1. customAn orange-red clear solution was obtained
  2. filtrationthe precipitate was filtered off
  3. washwashed with water (2×10 ml)
  4. customAfter drying in a high vacuum

출처 및 근거

ORD 기록
ord-64a2f03792b14a8b9bffc030ed2c4c3d
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710178B2

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