1,4-Dioxane → ethyl 2-[(1S,2S,4R)-bicyclo[2.2.1]hept-2-ylamino]-4-isopropylpyrimidine-5-carboxylate
Reaction equation
[CH:1]([C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][N:7]=[C:6](S(C)(=O)=O)[N:5]=1)([CH3:3])[CH3:2].Cl.[C@@H:20]12[CH2:26][C@@H:23]([CH2:24][CH2:25]1)[CH2:22][C@@H:21]2[NH2:27].O1CCOCC1.C(N(CC)C(C)C)(C)C>O>[C@@H:20]12[CH2:26][C@@H:23]([CH2:24][CH2:25]1)[CH2:22][C@@H:21]2[NH:27][C:6]1[N:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][N:7]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of ethyl 4-isopropyl-2-(methylsulfonyl)pyrimidine-5-carboxylate (400 mg), (1S,2S,4R)-bicyclo[2.2.1]heptan-2-aminehydrochloride (347 mg), and 1,4-dioxane (8 mL) was added N,N-diisopropyl ethylamine (1 mL) at room temperature, followed by stirring at the same temperature for 16 hours. To the reaction mixture was added water, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate) to obtain ethyl 2-[(1S,2S,4R)-bicyclo[2.2.1]hept-2-ylamino]-4-isopropylpyrimidine-5-carboxylate (417 mg) as a pale yellow solid.
Workup
- extractionthe aqueous layer was extracted with ethyl acetate
- washThe organic layer was washed with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)
Sources & evidence
- ORD record
- ord-7b364c9ee82940c7b984d470e17e8512
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524727B2
Reaction notes
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