Reaktion #3545

Reaktionsgleichung

4-amino-2-methylsulfanyl-pyrimidine-5-carbaldehyde

4-Amino-2-methylsulfanyl-pyrimidine-5-carboxaldehyde

2,6-dichlorophenylacetonitrile

sodium hydride

→

title compound

Ausbeute 32.1%

6-(2,6-Dichlorophenyl)-2-methylsulfanyl-pyrido-[2,3-d]pyrimidin-7-ylamine

Ausbeute 32.1%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was quenched with water
2. 2
   Extraktionextracted several times with dichloromethane
3. 3
   WaschenThe combined dichloromethane layers were washed with saturated sodium chloride
4. 4
   Trocknendried with magnesium sulfate
5. 5
   Einengenconcentrated in vacuo

Vorschrift

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+.

Quelle