Methylamine → HCID 58405769, Verbindung

HRID 44829

Reaktionsgleichung

[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([C:16]4[CH:21]=[CH:20][N:19]=[C:18](F)[CH:17]=4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:23])[C:8](=[O:24])[C@H:7]2[CH2:25][CH3:26])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:27][NH2:28]>CCN(CC)CC>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:28][CH3:27])[CH:17]=4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:23])[C:8](=[O:24])[C@H:7]2[CH2:25][CH3:26])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

Reaktionsbedingungen

Temperatur: 110 °C

Versuchsvorschrift

To a solution of (R)-8-cyclopentyl-7-ethyl-2-(2-fluoropyridin-4-yl)-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 16, 200 mg, 0.56 mmol) in methylamine (5 mL of 2M in CH3OH), 1 mL of Et3N was added. The mixture was stirred at 110° C. in a sealed tube for 18 h, and then concentrated under reduced pressure, quenched with water and extracted with EtOAc. The combined organic phase was dried with Na2SO4, concentrated under reduced pressure, and chromatographed (CH2Cl2:CH3OH=10:1) to give the title compound as a white solid (150 mg, 70% yield). 1H NMR (CDCl3) δ: 9.76 (broad, 1H), 8.08 (s, 1H) 7.85 (d, 1H), 7.74 (s, 1H), 7.58 (d, 1H), 4.40 (m, 2H), 3.43 (s, 3H), 3.1 (s, 3H), 2.2-1.7 (m, 10H) and 0.89 ppm (t, 3H); LCMS: 367.2 m/z (M+H)+; ret. Time: 1.44 min (Analytical Method E).

Aufarbeitung

concentrationconcentrated under reduced pressure
customquenched with water
extractionextracted with EtOAc
dry with materialThe combined organic phase was dried with Na2SO4
concentrationconcentrated under reduced pressure
customchromatographed (CH2Cl2:CH3OH=10:1)

Quellen und Nachweise

ORD-Eintrag: ord-f2c472cc80c14b8fa1ff403c98af04ae
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08541418B2

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