Potassium Carbonate → 2-Methyl-5-(4-o-tolyl-piperazin-1-ylmethyl)-pyrimidin-4-ylamine

HRID 2294001

Reaktionsgleichung

Reaktionsgleichung von HRID 2294001
Cl.Cl[CH2:3][C:4]1[C:5]([NH2:11])=[N:6][C:7]([CH3:10])=[N:8][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl.[C:20]1([CH3:32])[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>CN(C)C=O>[CH3:10][C:7]1[N:6]=[C:5]([NH2:11])[C:4]([CH2:3][N:29]2[CH2:30][CH2:31][N:26]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH3:32])[CH2:27][CH2:28]2)=[CH:9][N:8]=1

Komponenten

5

Edukt 3

HCID 11430Potassium Carbonate2×HCID 919641-(o-Tolyl)piperazine dihydrochlorideHCID 214736115-(Chloromethyl)-2-methylpyrimidin-4-amine--hydrogen chloride (1/1)

Produkt 1

HCID 214736052-Methyl-5-(4-o-tolyl-piperazin-1-ylmethyl)-pyrimidin-4-ylamineAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A suspension of 7.7 g (0.040 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine hydrochloride in 6 ml of dimethyl-formamide was treated with 15 g (0.11 mol) of dry potassium carbonate. At the same time a suspension of 10 g (0.040 mol) of 1-o-tolyl-piperazine dihydrochloride was treated with 15 g (0.11 mol) of dry potassium carbonate in 60 ml of dimethylformamide. After stirring at room temperature for 1/2 hr both solutions were combined and stirred for a further 4 hours. The reaction mixture was suction filtered, the residue was chromatographed over silica gel with dichloromethane/ethyl acetate 1:1 as the eluent and recrystallized from ethanol/ethyl acetate. 2.5 g of 2-methyl-5-(4-o-tolyl-piperazin-1-ylmethyl)-pyrimidin-4-ylamine were obtained as beige crystals; m.p. 189°-190°.

Aufarbeitung

  1. stirringstirred for a further 4 hours
  2. filtrationfiltered
  3. customthe residue was chromatographed over silica gel with dichloromethane/ethyl acetate 1:1 as the eluent
  4. customrecrystallized from ethanol/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b1ca3bbe4a98428d894c841811114531
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05688798

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