Ammonium Chloride → 4-(2-Butynyloxy)-5-fluoro-6-(2,5-dimethyl-1-pyrrolidinyl)pyrimidine
Reaction equation
[CH2:1]([O:5][C:6]1[C:11]([F:12])=[C:10](Cl)[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4].[CH3:14][CH:15]1[CH2:19][CH2:18][CH:17]([CH3:20])[NH:16]1.[Cl-].[NH4+]>>[CH2:1]([O:5][C:6]1[C:11]([F:12])=[C:10]([N:16]2[CH:17]([CH3:20])[CH2:18][CH2:19][CH:15]2[CH3:14])[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4]Participants
4
Procedure
0.2 g of 4-(2-butynyloxy)-6-chloro-5-fluoropyrimidine and 0.30 g of 2,5-dimethylpyrrolidine were mixed and left for 18 hours at room temperature. Into the reaction mixture was added a saturated ammonium chloride aqueous solution, and the mixture was extracted with tert-butyl methyl ether three times. The organic layers were washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.25 g of 4-(2-butynyloxy)-5-fluoro-6-(2,5-dimethyl-1-pyrrolidinyl)pyrimidine (hereinafter, referred to as Compound (6)).
Workup
- extractionthe mixture was extracted with tert-butyl methyl ether three times
- washThe organic layers were washed with a saturated sodium chloride aqueous solution
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c0794d0d8fe54a99b7d331cf51b7d0e9
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732448B2
Reaction notes
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