Potassium Carbonate → HCID 178418728, compound

HRID 989017Notes

Reaction equation

HRID 989017 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) δ0.91 (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-1a080ea7373d40fc9e7c805c9aa2e297
Source dataset
uspto-grants-2003_10
Patent number
US06638926B2

Reaction notes

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