Potassium Carbonate → 2-methyl-5-[(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)methyl]-4-pyrimidinamine

HRID 2294003

Reaction equation

HRID 2294003 reaction equation
Cl.Cl[CH2:3][C:4]1[C:5]([NH2:11])=[N:6][C:7]([CH3:10])=[N:8][CH:9]=1.Cl.[C:13]1([C:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH:24]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:13]1([C:19]2[CH2:24][CH2:23][N:22]([CH2:3][C:4]3[C:5]([NH2:11])=[N:6][C:7]([CH3:10])=[N:8][CH:9]=3)[CH2:21][CH:20]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27238604-Phenyl-1,2,3,6-tetrahydropyridine hydrochlorideHCID 214736115-(Chloromethyl)-2-methylpyrimidin-4-amine--hydrogen chloride (1/1)

Product 1

HCID 167591752-methyl-5-[(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)methyl]-4-pyrimidinamineYield 21.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 9.7 g (0.050 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine hydrochloride, 9.8 g (0.050 mol) of 4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride and 13.8 g (0.1 00 mol) of dry potassium carbonate in 125 ml of dimethylformamide was stirred vigorously at 80° for 5 hours. The mixture was cooled, suction filtered, completely freed from the solvents and the residue was triturated in water. The resulting crystals were filtered off under suction and recrystallized from ethanol/water. 3.0 g (21%) of 5-(4-phenyl-3,6-dihydro-2H-pyridin-1-ylmethyl)-2-methyl-pyrimidin-4-ylamine were obtained as yellow crystals; m.p. 165°-166°.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationsuction filtered
  3. customthe residue was triturated in water
  4. filtrationThe resulting crystals were filtered off under suction
  5. customrecrystallized from ethanol/water

Sources & evidence

ORD record
ord-3829ce9de2494c4895312378d13931eb
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Linked notes

Loading…