Hydrochloric Acid → 1-methyl-2-[1-(2-piperidin-4-yl-ethyl)piperidin-4-yloxy]-1H-[4,4']bipyrimidinyl-6-one
Reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[O:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH:24]2[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]2)[CH2:18][CH2:17]1.Cl>C(O)C>[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:4]=[C:3]1[O:15][CH:16]1[CH2:17][CH2:18][N:19]([CH2:22][CH2:23][CH:24]2[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]2)[CH2:20][CH2:21]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of tert-butyl 4-{2-[4-(1-methyl-6-oxo-1,6-dihydro-[4,4]bipyrimidinyl-2-yloxy)piperidin-1-yl]ethyl}piperidine-1-carboxylate (326 mg, 0.654 mmol) in ethanol (6.54 ml) was added 2N hydrogen chloride in ethanol (9.81 ml, 19.6 mmol) at room temperature. The mixture was stirred at room temperature for 3 hours. After concentration under reduced pressure, the residue was dissolved into water. The aqueous solution was washed with ethyl acetate and basified with potassium carbonate. Extraction with chloroform was performed three times. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford 1-methyl-2-[1-(2-piperidin-4-yl-ethyl)piperidin-4-yloxy]-1H-[4,4′]bipyrimidinyl-6-one as pale yellow solid (207 mg, 0.519 mmol, 79%).
Workup
- concentrationAfter concentration under reduced pressure
- dissolutionthe residue was dissolved into water
- washThe aqueous solution was washed with ethyl acetate
- extractionExtraction with chloroform
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-11a77e15f3a143d9b0e98abeacb62689
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006232B2
Reaction notes
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