Sodium hydride → HCID 22599868, compound
Reaction equation
[H-].[Na+].[F:3][C:4]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6].Cl[C:13]1[CH:18]=[C:17]([O:19][CH2:20][C:21]#[C:22][CH3:23])[N:16]=[CH:15][N:14]=1.[Cl-].[NH4+]>O1CCCC1>[F:3][C:4]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][C:13]1[CH:18]=[C:17]([O:19][CH2:20][C:21]#[C:22][CH3:23])[N:16]=[CH:15][N:14]=1Participants
Procedure
In 4 ml of tetrahydrofuran was suspended 0.33 g of sodium hydride (60% in oil), to which 0.6 ml of a tetrahydrofuran solution containing 0.42 g of 2,3-difluoroaniline were slowly added dropwise with stirring at room temperature. The mixture was stirred at room temperature for 20 minutes, to which 1 ml of a tetrahydrofuran solution containing 0.5 g of 4-chloro-6-(2-butynyloxy)pyrimidine was slowly added dropwise, followed by stirring at room temperature for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with chloroform. The chloroform layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.25 g of 4-(N-(2,3-difluorophenyl)amino)-6-(2-butynyloxy)pyrimidine (the present compound (73)), m.p.: 147.6° C.
Workup
- additionwere slowly added dropwise
- additionwas slowly added dropwise
- stirringby stirring at room temperature for 4 hours
- extractionextracted three times with chloroform
- washwashed with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-48a2d53e7ef442b3859ccd3e4a471746
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07291730B2
Reaction notes
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