2-Methyl-2-thiopseudourea sulfate → Tert-butyl 2-(methylthio)-5H-pyrrolo[3,4-D]pyrimidine-6(7H)-carboxylate
Reaktionsgleichung
S(O)(O)(=O)=O.[CH3:6][S:7][C:8](=[NH:10])[NH2:9].[O-]CC.[Na+].CN([CH:18]=[C:19]1[C:23](=O)[CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20]1)C>C(O)C>[CH3:6][S:7][C:8]1[N:9]=[CH:18][C:19]2[CH2:20][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22][C:23]=2[N:10]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a solution of 2-methyl-2-thiopseudourea sulfate (3.5 g, 25 mmol) in ethanol at 0° C. was added a solution of sodium ethoxide (9.6 mL, 21%). After stirring for 10 min, a solution of tert-butyl 3-[(dimethylamino)methylene]-4-oxopyrrolidine-1-carboxylate (2.0 g, 8.32 mmol) in ethanol was added, and the mixture was heated at 80° C. for 1 h. Additional 2-methyl-2-thiopseudourea sulfate (3.5 g, 25 mmol) and sodium ethoxide (9.6 mL, 21%) was added and heated at 80° C. for 1 h. The ethanol was removed under reduced pressure, the residue was diluted with ethyl acetate (400 mL), washed with saturated aqueous sodium bicarbonate, brine, dried over sodium sulfate, and concentrated. The residue was purified on a Biotage silica gel cartridge (gradient 10-35% ethyl acetate in hexanes) to yield tert-butyl 2-(methylthio)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate.
Aufarbeitung
- temperatureheated at 80° C. for 1 h
- customThe ethanol was removed under reduced pressure
- additionthe residue was diluted with ethyl acetate (400 mL)
- washwashed with saturated aqueous sodium bicarbonate, brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customThe residue was purified on a Biotage silica gel cartridge (gradient 10-35% ethyl acetate in hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-2fcde099a1d449219575aa90174e55d9
- Quelldatensatz
- uspto-grants-2011_03
- Patentnummer
- US07906649B2
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