2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole → 2-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-[2-(3-pyridyl)ethyl]-4-pyrimidone
Reaktionsgleichung
[CH3:1][N:2]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])[N:9]=1)[CH3:3].CS[C:17]1[NH:22][C:21](=[O:23])[C:20]([CH2:24][CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[CH:19][N:18]=1>N1C=CC=CC=1>[CH3:3][N:2]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:17]2[NH:22][C:21](=[O:23])[C:20]([CH2:24][CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[CH:19][N:18]=2)[N:9]=1)[CH3:1]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Following the procedure of Example 12, a mixture of 1.29 g. of 2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethylamine and 1.37 g. of 2-methylthio-5-[2-(3-pyridyl)ethyl]-4-pyrimidone in 25 ml. of anhydrous pyridine was heated to refluxing temperature for about 4 days. The solvent was removed in vacuo. The residue was dissolved in ethanol and the ethanol evaporated. The residue was purified by high pressure liquid chromatography over silica using a gradient elution technique with an ethyl acetate/ethanol/ammonium hydroxide solvent system as the eluant. Fractions shown by tlc to contain the desired product were combined and the combined fractions rechromatographed on a silica preparative plate using 3% ammoniated ethanol as the solvent. 2-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-[2-(3-pyridyl)ethyl]-4-pyrimidone free base thus prepared was converted by standard procedures to the trihydrochloride salt which melted at 226°-228° C. after recrystallization from an ethanol/ethyl acetate/ether solvent mixture. Yield=1.0 g.