Potassium Carbonate → 1-(5-Nitro-2-pyrimidinyl)-3-piperidinol
Reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([OH:7])[CH2:2]1.Cl[C:9]1[N:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][N:10]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N+:15]([C:12]1[CH:11]=[N:10][C:9]([N:1]2[CH2:6][CH2:5][CH2:4][CH:3]([OH:7])[CH2:2]2)=[N:14][CH:13]=1)([O-:17])=[O:16]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a stirring solution of piperidin-3-ol (0.333 g, 3.29 mmol) and 2-chloro-5-nitropyrimidine (0.500 g, 3.13 mmol) in DMF (8 mL) was added K2CO3 (1.04 g, 7.52 mmol). The resulting yellowish suspension was stirred at 70° C. for 1.5 h. After this time, LC/MC showed the reaction was complete. The reaction mixture was allowed to cool to rt, then partitioned between water and EtOAc. The separated aqueous phase was extracted with EtOAc (2×). The combined EtOAc extracts were washed with water (1×), saturated aqueous NaCl (2×). The organic layer was dried over Na2SO4, filtered and concentrated. The residue was dried in vacuum for 30 min to afford the desired product 1-(5-nitropyrimidin-2-yl)piperidin-3-ol (536 mg, 2.391 mmol, 76% yield) as a yellow solid. Anal. Calcd. for C9H12N4O3 m/z 224.2, found: 225.1 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 9.17-8.91 (m, 2H), 4.20 (dd, J=13.14, 3.03 Hz, 1H), 4.03 (ddd, J=13.07, 7.14, 3.79 Hz, 1H), 3.96-3.74 (m, 2H), 2.95 (s, 1H), 2.11-1.87 (m, 2H), 1.81-1.50 (m, 3H).
Workup
- temperatureto cool to rt
- custompartitioned between water and EtOAc
- extractionThe separated aqueous phase was extracted with EtOAc (2×)
- washThe combined EtOAc extracts were washed with water (1×), saturated aqueous NaCl (2×)
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was dried in vacuum for 30 min
Sources & evidence
- ORD record
- ord-4fd91cd557b244999ba20b40fe4502a4
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710049B2
Reaction notes
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