Potassium Carbonate → HCID 178418728, compound

HRID 2121459Notes

Reaction equation

HRID 2121459 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH3:14])[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.[NH2:15][C:16]1[NH:17][N:18]=[C:19]([CH3:21])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)CCC>[CH3:14][CH:11]1[CH2:12][CH2:13][N:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:15][C:16]3[NH:17][N:18]=[C:19]([CH3:21])[CH:20]=3)[N:7]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 219392272-Chloro-4-(4-methylpiperidin-1-yl)pyrimidineHCID 178418690HCID 178418690, compound

Product 1

HCID 178418728HCID 178418728, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of 2-chloro-4-(4-methylpiperidin-1-yl)-pyrimidine (prepared using a procedure similar to the one reported in Eur. J. Med. Chem., 26(7) 729(1991))(222 mg, 1.05 mmol) in BuOH (5 mL) was added 3-amino-5-methyl-2H-pyrazole (305 mg, 3.15 mmol) and the reaction mixture was then heated under reflux overnight. The solvent was evaporated and the residue dissolved in a mixture ethanol/water (1/3, 4 mL). Potassium carbonate (57 mg, 0.41 mmol) was added and the mixture was stirred at room temperature for 2 hours. The resulting suspension was filtered, washed with water twice and rinsed with ether twice to give the title compound as a white solid (143 mg, 50%): mp 193-195° C.; 1H NMR (DMSO) 67 0.91 (3H, d), 1.04 (2H, m), 1.67 (3H, m), 2.16 (3H, s), 2.83 (2H, t), 4.31 (2H, m), 6.19 (2H, m), 7.87 (1H, d), 8.80 (1H, br s), 11.71 (1H, s); IR (solid) 1627, 1579, 1541, 1498, 1417, 1388, 1322, 1246; MS 273.3(M+H)+.

Workup

  1. temperaturethe reaction mixture was then heated
  2. temperatureunder reflux overnight
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in a mixture ethanol/water (1/3, 4 mL)
  5. filtrationThe resulting suspension was filtered
  6. washwashed with water twice
  7. washrinsed with ether twice

Sources & evidence

ORD record
ord-766cb856f058407d8b57098caabed2d2
Source dataset
uspto-grants-2004_02
Patent number
US06696452B2

Reaction notes

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