Potassium Carbonate → 5-[4-(4-fluoro-phenyl)-3,6-dihydro-2H-pyridin-1-ylmethyl]-2-methyl-pyrimidin-4-ylamine

HRID 2294004

Reaction equation

HRID 2294004 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.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH2:21][CH2:22][NH:23][CH2:24][CH:25]=2)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH2:25][CH2:24][N:23]([CH2:3][C:4]3[C:5]([NH2:11])=[N:6][C:7]([CH3:10])=[N:8][CH:9]=3)[CH2:22][CH:21]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1977474-(4-Fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochlorideHCID 214736115-(Chloromethyl)-2-methylpyrimidin-4-amine--hydrogen chloride (1/1)

Product 1

HCID 214736285-[4-(4-fluoro-phenyl)-3,6-dihydro-2H-pyridin-1-ylmethyl]-2-methyl-pyrimidin-4-ylamineYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 27.2 g (0.14 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine hydrochloride, 29.8 g (0.14 mol) of 4-(4-fluoro-phenyl)-1,2,3,6-tetrahydropyridine hydrochloride and 42 g (0.30 mol) of dry potassium carbonate in 200 ml of dimethyl-formamide was stirred at room temperature for 18 hours. The mixture was suction filtered, the filter cake was washed with dichloromethane, the filtrate was completely freed from the solvents and the residue was crystallized twice from ethyl acetate/cyclohexane. 11.6 g (28%) of 5-[4-(4-fluoro-phenyl)-3,6-dihydro-2H-pyridin-1-ylmethyl]-2-methyl-pyrimidin-4-ylamine were obtained as yellowish crystals; m.p. 176°-178°.

Workup

  1. filtrationfiltered
  2. washthe filter cake was washed with dichloromethane
  3. customthe residue was crystallized twice from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-a6b760196417413bb732954c365e53c3
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Linked notes

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