Hydrochloric Acid → Tert-butyl 3-amino-3-(pyrimidin-2-yl)azetidine-1-carboxylate hydrochloride

HRID 509559Notizen

Reaktionsgleichung

CC(C)(S([NH:6][C:7]1([C:18]2[N:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8]1)=O)C.[ClH:25].CCOCC>CO>[ClH:25].[NH2:6][C:7]1([C:18]2[N:19]=[CH:20][CH:21]=[CH:22][N:23]=2)[CH2:8][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:10]1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

tert-Butyl 3-(1,1-dimethylethylsulfinamido)-3-(pyrimidin-2-yl)azetidine-1-carboxylate (40 mg, 0.113 mmol) in MeOH (0.5 ml) in a 10 ml round-bottomed flask was cooled to 0° C. A solution of HCl in ether (0.141 ml, 0.564 mmol, 4 N) was added. The mixture was then stirred at 0° C. for 15 min and then concentrated at room temperature. The residue was triturated with hexane and diethyl ether. The resulting solid was allowed to settle and supernatant liquid was decanted. The solid obtained was dried under vacuo to afford tert-butyl 3-amino-3-(pyrimidin-2-yl)azetidine-1-carboxylate hydrochloride Yield: 28 mg (87%). 1H NMR (400 MHz, DMSO-d6): δ 9.08 (bs, 2H), 9.0 (d, J=4.8 Hz, 2H), 7.63 (t, J=4.8 Hz, 1H), 4.23-4.21 (m, 4H), 1.43 (s, 9H). LCMS: (ES+) m/z observed=151.2 (M+H)+ of 3-(pyrimidin-2-yl)azetidin-3-amine

Aufarbeitung

concentrationconcentrated at room temperature
customThe residue was triturated with hexane and diethyl ether
customsupernatant liquid was decanted
customThe solid obtained
customwas dried under vacuo

Quellen und Nachweise

ORD-Eintrag: ord-2f47f937b80447858d59117c9582a936
Quelldatensatz: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09096580B2

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