Tert-butyl {6-[3-(2-methyl-5-nitro-phenyl)-1-methyl-ureido]-pyrimidin-4-yl}-carbamate → tert-Butyl {6-[3-(5-Amino-2-methyl-Phenyl)-1-methyl-ureido]-pyrimidin-4-yl}-carbamate
Reaktionsgleichung
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[NH:11][C:12](=[O:29])[N:13]([C:15]1[N:20]=[CH:19][N:18]=[C:17]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:16]=1)[CH3:14]>CO.CN(C=O)C.[Pd]>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([NH:11][C:12](=[O:29])[N:13]([C:15]2[N:20]=[CH:19][N:18]=[C:17]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH:16]=2)[CH3:14])[CH:4]=1Komponenten
5
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Versuchsvorschrift
A solution of tert-butyl {6-[3-(2-methyl-5-nitro-phenyl)-1-methyl-ureido]-pyrimidin-4-yl}-carbamate (330 mg, 0.82 mmol) in a mixture of methanol (20 ml) and DMF (50 ml) is hydrogenated in the presence of 10% palladium on charcoal (500 mg) at atmospheric pressure. After 20 h the hydrogenation is complete and the catalyst is filtered off. The filtrate is evaporated to dryness. The residue obtained is triturated with ether, filtered off, and vacuum dried to afford a gray powder: HPLC: tR=5.38 min (purity: 97%, gradient A), ESI-MS: 373.4 [MH]+.
Aufarbeitung
- filtrationthe catalyst is filtered off
- customThe filtrate is evaporated to dryness
- customThe residue obtained
- customis triturated with ether
- filtrationfiltered off
- customvacuum dried
- customto afford a gray powder
Quellen und Nachweise
- ORD-Eintrag
- ord-96aaa287cc554197b10fc9f6f7acebae
- Quelldatensatz
- uspto-grants-2013_10
- Patentnummer
- US08552002B2
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