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

HRID 1369963

反応式

HRID 1369963 の反応式
[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

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 10219456N-cyano-N-methylmethanesulphonamideHCID 178500902HCID 178500902、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ba404f0fb2204f88a6df4bb4afb1b514
出典データセット
uspto-grants-2003_06
特許番号
US06579984B1

関連ノート

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