Guanidine Hydrochloride → 4'-Methyl-2-methylsulfanyl-[4,5']bipyrimidinyl-2'-ylamine
Reaktionsgleichung
CN(C)[CH:3]=[C:4]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]([S:14][CH3:15])[N:9]=1)[C:5](=O)[CH3:6].C([O-])([O-])=O.[K+].[K+].Cl.[NH2:24][C:25]([NH2:27])=[NH:26]>CN(C=O)C>[CH3:6][C:5]1[C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([S:14][CH3:15])[N:9]=2)=[CH:3][N:24]=[C:25]([NH2:27])[N:26]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
To a solution of 4-Dimethylamino-3-(2-methylsulfanyl-pyrimidin-4-yl)-but-3-en-2-one (18) (1.02 g, 4.30 mmol) in DMF (14 mL) was added K2CO3 (1.782 g, 12.89 mmol) and Guanidine HCl (0.616 g, 6.45 mmol) and the resulting suspension was stirred at 120° C. for 1 hour. The DMF was evaporated and the crude residue partitioned between water and ethyl acetate. The organic layer was washed with water and brine, dried with sodium sulfate, and concentrated. The crude residue was purified by flash chromatography with a gradient of 1-12% MeOH in DCM to give the desired product as a light yellow solid (800 mg, 80%). MS (ES+): m/z=234.3/235.4 (100/20) [MH+]. HPLC: tR=1.01 minutes over 3 minutes. Purity: 70% [HPLC (LC/MS) at 220 nm].
Aufarbeitung
- customThe DMF was evaporated
- customthe crude residue partitioned between water and ethyl acetate
- washThe organic layer was washed with water and brine
- dry with materialdried with sodium sulfate
- concentrationconcentrated
- customThe crude residue was purified by flash chromatography with a gradient of 1-12% MeOH in DCM
Quellen und Nachweise
- ORD-Eintrag
- ord-025e070e01ca447cbb1ff1508aaefbdb
- Quelldatensatz
- uspto-grants-2014_12
- Patentnummer
- US08901147B2
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