Reaktionsgleichung
[CH3:1][O:2][CH:3]([C:8]([O:10]C)=O)[C:4]([O:6]C)=O.Cl.[CH2:13]([O:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH2:27])=[NH:26])=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[OH:6][C:4]1[C:3]([O:2][CH3:1])=[C:8]([OH:10])[N:27]=[C:25]([C:24]2[CH:28]=[CH:29][C:21]([O:20][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:22][CH:23]=2)[N:26]=1Komponenten
Versuchsvorschrift
In process (A), dimethyl methoxymalonate and 4-benzyloxybenzamidine hydrochloride are reacted to obtain 4,6-dihydroxy-5-methoxy-2-(4-benzyloxyphenyl)pyrimidine (1), which is then chlorinated with phosphorus oxychloride to obtain a dichloro derivative (2). The compound (2) is debenzylated by hydrogenation using palladium-on-carbon to obtain 5-methoxy-2-(4-hydroxyphenyl)pyrimidine (3), which is again protected with a benzyl group [(3)→(4)], followed by demethylation [(4)→(5)]. Compound (5) is reacted with an optically active 3-fluoroalkyl mesylate to obtain compound (6). After removing the benzyl protective group by hydrogenation with palladium-on-carbon [(6)→(7)], compound (7) is reacted with an optically active 3-fluoroalkyl mesylate to obtain compound (8).
Quellen und Nachweise
- ORD-Eintrag
- ord-64e177681001444f9d2b40235ad62195
- Quelldatensatz
- uspto-grants-1994_03
- Patentnummer
- US05290477
Verknüpfte Notizen
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