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

HRID 509559Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

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

Workup

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

Sources & evidence

ORD record: ord-2f47f937b80447858d59117c9582a936
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096580B2

Reaction notes

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