1,4-Dioxane hydrochloride → N2-(3-chlorophenyl)-4-(trifluoromethyl)pyrimidine-2,5-diamine
Reaction equation
C(OC(=O)[NH:7][C:8]1[C:9]([C:22]([F:25])([F:24])[F:23])=[N:10][C:11]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[N:12][CH:13]=1)(C)(C)C.O1CCOCC1.Cl>O1CCOCC1>[Cl:21][C:17]1[CH:16]=[C:15]([NH:14][C:11]2[N:10]=[C:9]([C:22]([F:24])([F:25])[F:23])[C:8]([NH2:7])=[CH:13][N:12]=2)[CH:20]=[CH:19][CH:18]=1Participants
Procedure
To a mixture of tert-butyl{2-[(3-chlorophenyl)amino]-4-(trifluoromethyl)pyrimidin-5-yl}carbamate (267 mg) and 1,4-dioxane (3 mL) was added a 4 M hydrogen chloride-1,4-dioxane solution (3 mL), followed by stirring at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure, and to the obtained residue was added a saturated aqueous sodium hydrogen carbonate solution (20 mL), followed by extraction with ethyl acetate (50 mL). The extract was washed with saturated brine (20 mL), and the organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: chloroform-methanol) to obtain N2-(3-chlorophenyl)-4-(trifluoromethyl)pyrimidine-2,5-diamine (180 mg) as a yellow solid.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionto the obtained residue was added a saturated aqueous sodium hydrogen carbonate solution (20 mL)
- extractionfollowed by extraction with ethyl acetate (50 mL)
- washThe extract was washed with saturated brine (20 mL)
- dry with materialthe organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (eluent: chloroform-methanol)
Sources & evidence
- ORD record
- ord-1c7fd542af5b432f8ef622f6e5811ca1
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524727B2
Reaction notes
Loading…