Ethyl 4-amino-1-piperidinecarboxylate → 4-[4-Amino-5-(2-methoxybenzoyl)pyrimidin-2-ylamino]piperidine-1-carboxylic Acid Ethyl Ester
Reaction equation
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[O:9])=[CH:6][N:5]=[C:4](S(CC)(=O)=O)[N:3]=1.[NH2:23][CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:26][CH2:25]1>C(O)(C)C>[CH2:33]([O:32][C:30]([N:27]1[CH2:26][CH2:25][CH:24]([NH:23][C:4]2[N:3]=[C:2]([NH2:1])[C:7]([C:8](=[O:9])[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[O:16][CH3:17])=[CH:6][N:5]=2)[CH2:29][CH2:28]1)=[O:31])[CH3:34]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 105 °C
Procedure
A suspension of (4-amino-2-ethanesulfonylpyrimidin-5-yl)-(2-methoxyphenyl)-methanone (20.0 mg, 0.0650 mmol, Example 6) and ethyl 4-amino-1-piperidinecarboxylate (15.1 mg, 0.0876 mmol, Aldrich) in isopropanol (2.5 mL) was placed in a sealed tube and heated at ˜100-110° C. under microwave conditions for ˜1 hour and the resulting mixture was evaporated in vacuo. The crude product was purified on silica gel with 95:5 of dichloromethane/methanol to give 4-[4-amino-5-(2-methoxy-benzoyl)-pyrimidin-2-ylamino]-piperidine-1-carboxylic acid ethyl ester as a light yellow solid (22.1 mg, 89% yield). HRMS, observed: 400.1984; Calcd for (M+H)+: 400.1980.
Workup
- customwas placed in a sealed tube
- customthe resulting mixture was evaporated in vacuo
- customThe crude product was purified on silica gel with 95:5 of dichloromethane/methanol
Sources & evidence
- ORD record
- ord-4f203a24f3a14630b3d9a537009f8619
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07615634B2
Reaction notes
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