Diisopropylethylamine → 2-chloro-4-methyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one
Reaktionsgleichung
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([NH2:9])=[C:4]([CH3:10])[N:3]=1.Cl.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH:13]1[C:18](O)=[O:19].CCN(C(C)C)C(C)C>CS(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([CH3:10])[C:5]2[NH:9][C:18](=[O:19])[CH:13]3[CH2:14][O:15][CH2:16][CH2:17][N:12]3[C:6]=2[N:7]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
A round-bottom flask was charged with crude 2,4-dichloro-6-methylpyrimidin-5-amine (6.644 g, 37.3 mmol), morpholine-3-carboxylic acid hydrochloride (7.51 g, 44.8 mmol), DIPEA (26.1 mL, 149 mmol) and DMSO (49.0 mL). The flask was heated overnight at 100° C. The mixture was subsequently cooled to room temperature and then poured into ice. The solution was stirred while slowly warmed to room temperature. The mixture was subsequently filtered, and the filtrate was purified by preparatory HPLC using a gradient of 15-40% CH3CN (with 0.035% TFA) in H2O (with 0.05% TFA). The fractions were collected and concentrated in vacuo to give the title compound as a white solid (387 mg, 4.1%). 1H NMR (400 MHz, DMSO-d6) δ 2.26 (s, 3H), 2.54 (s, 1H), 2.87-2.99 (m, 1H), 3.43-3.52 (m, 1H), 3.91 (dd, J=11.72, 3.42 Hz, 1H), 4.10-4.22 (m, 2H), 4.29 (dd, J=10.74, 3.91 Hz, 1H), 10.51 (s, 1H). ESI-MS m/z [M+H]+ calc'd for C10H11ClN4O2, 255.06. found 255.5.
Aufarbeitung
- temperatureThe mixture was subsequently cooled to room temperature
- additionpoured into ice
- temperaturewhile slowly warmed to room temperature
- filtrationThe mixture was subsequently filtered
- customthe filtrate was purified by preparatory HPLC
- customThe fractions were collected
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-b7fed352730f4190a033895edab2eb88
- Quelldatensatz
- uspto-grants-2014_07
- Patentnummer
- US08791107B2
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