Sodium hydride → 6-(2,6-Dichlorophenyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7-amine
Reaction equation
[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]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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+.
Workup
- customthe reaction was quenched with water
- extractionextracted several times with dichloromethane
- washThe combined dichloromethane layers were washed with saturated sodium chloride
- dry with materialdried with magnesium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b111cf303a024297af1a1c76953ad858
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05952342
Reaction notes
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