Diisopropylethylamine → (S)-3-(2-((S)-1-cyclopropylethylamino)-5-fluoropyrimidin-4-yl)-4-phenyloxazolidin-2-one

HRID 1850236Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][O:10][C:9]2=[O:19])[C:5]([F:20])=[CH:4][N:3]=1.[CH:21]1([C@@H:24]([NH2:26])[CH3:25])[CH2:23][CH2:22]1.CCN(C(C)C)C(C)C>CS(C)=O.O>[CH:21]1([C@@H:24]([NH:26][C:2]2[N:7]=[C:6]([N:8]3[C@@H:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:11][O:10][C:9]3=[O:19])[C:5]([F:20])=[CH:4][N:3]=2)[CH3:25])[CH2:23][CH2:22]1

Participants

Conditions

Temperature: 127.5 °C

Procedure

A mixture of (S)-3-(2-chloro-5-fluoropyrimidin-4-yl)-4-phenyloxazolidin-2-one (40 mg, 0.136 mmol), (S)-1-cyclopropylethanamine (34.8 mg, 0.409 mmol), Hunig's Base (0.119 mL, 0.681 mmol) in DMSO (0.4 mL) was heated under argon at 105-115° C. for ˜18 hrs (alternative: 120-135° C. for ˜90 min). Then mixture was allowed to cool to room temperature. The mixture was diluted with DMSO and water (˜10 vol. % of DMSO), filtered through a syringe filter and purified by reverse phase HPLC. Selected fractions were collected and lyophilized providing (S)-3-(2-((S)-1-cyclopropylethylamino)-5-fluoropyrimidin-4-yl)-4-phenyloxazolidin-2-one (26 mg) as a white solid as its trifluoroacetic acid salt.

Workup

temperatureto cool to room temperature
filtrationfiltered through a syringe
filtrationfilter
custompurified by reverse phase HPLC
customSelected fractions were collected

Sources & evidence

ORD record: ord-b92f1f1d26f24e7687b7631026f216cd
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957068B2

Reaction notes

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