2-Amino-4-methylpyrimidine → 1,1-dimethylethyl (2S)-2-[(7-methylimidazo[1,2-a]pyrimidin-2-yl)methyl]-1-piperidinecarboxylate
Reaktionsgleichung
Br[CH2:2][C:3](=O)[CH2:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[CH3:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]([NH2:26])[N:21]=1>CN(C=O)C.[Cl-].[Na+].O>[CH3:19][C:20]1[CH:25]=[CH:24][N:23]2[CH:2]=[C:3]([CH2:4][C@@H:5]3[CH2:10][CH2:9][CH2:8][CH2:7][N:6]3[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:26]=[C:22]2[N:21]=1Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a solution of 1,1-dimethylethyl (2S)-2-(3-bromo-2-oxopropyl)-1-piperidinecarboxylate D2 (0.300 g, 0.94 mmol) in DMF (2 ml) was added 4-methyl-2-pyrimidinamine (0.153 g, 1.41 mmol) and the mixture was stirred at 80° C. for 1.5 h. To the reaction mixture was added brine and a saturated NaHCO3 aqueous solution and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered and evaporated and the residue was purified by flash cromatography on silica gel (Biotage 25+M, DCM/MeOH from 100/0 to 90/10). Collected fractions gave the title compound (0.350 g slightly contaminated with residual 4-methyl-2-pyrimidinamine). UPLC: rt=0.53, peak observed: 331 (M+1). C18H26N4O2 requires 330.
Aufarbeitung
- extractiona saturated NaHCO3 aqueous solution and extracted with EtOAc
- dry with materialThe organic layer was dried (Na2SO4)
- filtrationfiltered
- customevaporated
- customthe residue was purified by flash cromatography on silica gel (Biotage 25+M, DCM/MeOH from 100/0 to 90/10)
Quellen und Nachweise
- ORD-Eintrag
- ord-2bb197205037464a851dcc660e635c14
- Quelldatensatz
- uspto-grants-2012_01
- Patentnummer
- US08093255B2
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