4-(4,6-Dichloropyrimidin-2-yl)morpholine → HCID 86718537, compound

HRID 929955Notes

Reaction equation

[CH2:1]([C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[O:6][C:5](=[O:16])[NH:4]1)[CH3:2].[Cl:17][C:18]1[CH:23]=[C:22](Cl)[N:21]=[C:20]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[N:19]=1>CN(C=O)C>[Cl:17][C:18]1[N:19]=[C:20]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[N:21]=[C:22]([N:4]2[C@@H:3]([CH2:1][CH3:2])[C@H:7]([C:8]3[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=3)[O:6][C:5]2=[O:16])[CH:23]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of (4R*,5R*)-4-ethyl-5-(4-methoxyphenyl)oxazolidin-2-one (217 mg, 0.98 mmol) in DMF (2 mL) was added at room temperature under argon NaH (51.4 mg, 1.18 mmol). After 20 minutes, a suspension of 4-(4,6-dichloropyrimidin-2-yl)morpholine (230 mg, 0.98 mmol in DMF (1 mL) was added, and the reaction mixture was stirred at 85° C. for 20 minutes. The solution was quenched at 0° C. with aqueous NH4Cl, extracted with ethyl acetate, and the organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography using EtOAc in hexane from 0% to 20% in order to give the title compound as a white solid (375 mg, 91%). LC-MS: [M+H] 419.1; Rt 1.26 min; (LCMS method 1).

Workup

additionwas added
customThe solution was quenched at 0° C. with aqueous NH4Cl
extractionextracted with ethyl acetate
dry with materialthe organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by column chromatography

Sources & evidence

ORD record: ord-a10660097a894c2db926deaf1d67286e
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296733B2

Reaction notes

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