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

HRID 3449

Reaktionsgleichung

Reaktionsgleichung von HRID 3449
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 218500176-(2,6-Dichlorophenyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7-amineAusbeute 32,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e715d98ba3a64d67bf7124f153c54da7
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733913

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