Potassium Carbonate → 1-(4'-(Cyclopropylmethyl)-2-(methylthio)-4,5'-bipyrimidin-2'-ylamino)-2-methylpropan-2-ol
Reaktionsgleichung
[CH:1]1([CH2:4][C:5](=O)/[C:6](/[C:11]2[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=2)=[CH:7]\N(C)C)[CH2:3][CH2:2]1.[OH:20][C:21]([CH3:28])([CH3:27])[CH2:22][NH:23][C:24]([NH2:26])=[NH:25].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:1]1([CH2:4][C:5]2[C:6]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)=[CH:7][N:26]=[C:24]([NH:23][CH2:22][C:21]([CH3:28])([OH:20])[CH3:27])[N:25]=2)[CH2:2][CH2:3]1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
To a solution of (Z)-1-cyclopropyl-4-(dimethylamino)-3-(2-(methylthio)pyrimidin-4-yl)but-3-en-2-one (3) in DMF (4 mL), 1-(2-hydroxy-2-methylpropyl)guanidine (529 mg, 3.15 mmol) and potassium carbonate (872 mg, 6.31 mmol) were added, and the reaction mixture was stirred at 120° C. for 2 h. The reaction mixture was purified by a reverse-phase Gilson HPLC [30-90% organic phase over 15 min] followed by a Biotage silica gel chromatography [10 g SNAP column, 100% DCM to 12% MeOH/DCM] to obtain the desired product as a glassy solid (90 mg, 21% yield). MS (ES+): m/z=392.2/393.2/394.3 (100/40/10) [MH+]. HPLC: tR=1.12 min over 3 min. Purity: 100% [HPLC (LC/MS) at 220 nm].
Aufarbeitung
- customThe reaction mixture was purified by a reverse-phase Gilson HPLC [30-90% organic phase over 15 min]
Quellen und Nachweise
- ORD-Eintrag
- ord-8935a0400fe64253a354af7e88ec5537
- Quelldatensatz
- uspto-grants-2014_04
- Patentnummer
- US08685993B2
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