Potassium Carbonate → HCID 21473645, compound

HRID 2294031Notes

Reaction equation

HRID 2294031 reaction equation
Br.Br.Br[CH2:4][C:5]1[C:6]([NH2:14])=[N:7][C:8]([CH2:11][CH2:12][CH3:13])=[N:9][CH:10]=1.Cl.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH2:24][CH2:25][NH:26][CH2:27][CH:28]=2)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH2:28][CH2:27][N:26]([CH2:4][C:5]3[C:6]([NH2:14])=[N:7][C:8]([CH2:11][CH2:12][CH3:13])=[N:9][CH:10]=3)[CH2:25][CH:24]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1977474-(4-Fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochlorideHCID 21473668HCID 21473668, compound

Product 1

HCID 21473645HCID 21473645, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 7.0 g (0.020 mol) of 5-bromomethyl-2-propyl-pyrimidin-4-ylamine dihydrobromide, 4.2 g (0.020 mol) of 4-(4-fluoro-phenyl)-1,2,3,6-tetrahydropyridine hydrochloride and 8.0 g (0.060 mol) of dry potassium carbonate in 60 ml of dimethylformamide 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 recrystallized twice from ethyl acetate/cyclohexane and then from hot ethanol. 1.4 g (21%) of 5-[4-(4-fluoro-phenyl)-3,6-dihydro-2H-pyridin-1-ylmethyl]-2-propyl-pyrimidin-4-ylamine were obtained as white crystals; m.p. 142°-145°.

Workup

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

Sources & evidence

ORD record
ord-ae2c5862eac149559da4265b4b9144dc
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

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