Sodium hydride → 6-(2,6-Dichlorophenyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7-amine

HRID 3449

反応式

HRID 3449 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]#[N:11].[H-].[Na+].[NH2:14][C:15]1[C:20]([CH:21]=O)=[CH:19][N:18]=[C:17]([S:23][CH3:24])[N:16]=1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:10]([NH2:11])=[N:14][C:15]2[N:16]=[C:17]([S:23][CH3:24])[N:18]=[CH:19][C:20]=2[CH:21]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 76678(2,6-Dichlorophenyl)acetonitrileHCID 2957694-Amino-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

生成物 1

HCID 218500176-(2,6-Dichlorophenyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7-amine収率 32.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Into a solution of 2,6-dichlorophenylacetonitrile (0.55 g) in dimethylformamide (5 mL) was added one equivalent of 60% sodium hydride suspension (0.12 g). After 10 minutes, 4-amino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (0.50 g) obtained from Example 76 was added. After stirring overnight at room temperature, the reaction was quenched with water. The aqueous solution was acidified with 1N hydrochloric acid to a pH of 7 and extracted several times with dichloromethane. The combined dichloromethane layers were washed with saturated sodium chloride, dried with magnesium sulfate, and concentrated in vacuo. Chromatography of this residue down silica gel with ethyl acetate:hexane (2:1) gave 0.32 g of the title compound, CIMS (1% NH3 in CH4): 365=M+ +C2H5, 337=M+ +H (Base), 336=M+.

後処理

  1. customthe reaction was quenched with water
  2. extractionextracted several times with dichloromethane
  3. washThe combined dichloromethane layers were washed with saturated sodium chloride
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e715d98ba3a64d67bf7124f153c54da7
出典データセット
uspto-grants-1998_03
特許番号
US05733913

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