Ethyl Acrylate → 2-(4-Cyclohexyl-phenoxymethyl)-2,3,5,6-tetrahydro-oxazolo[3,2-a]pyrimidin-7-one

HRID 237755Notes

Reaction equation

[CH:1]1([C:7]2[CH:20]=[CH:19][C:10]([O:11][CH2:12][CH:13]3[O:17][C:16]([NH2:18])=[N:15][CH2:14]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:21](OCC)(=[O:24])[CH:22]=[CH2:23].CCCCCCC>C(O)C.C(Cl)Cl>[CH:1]1([C:7]2[CH:20]=[CH:19][C:10]([O:11][CH2:12][CH:13]3[O:17][C:16]4=[N:18][C:21](=[O:24])[CH2:22][CH2:23][N:15]4[CH2:14]3)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine (350 mg, 1.28 mmol) in ethanol (6 mL) was added ethyl acrylate (255.8 mg, 2.56 mmol). The reaction mixture was heated in a microwave oven at 150° C. for 40 min. The solvent was removed under vacuum, and the residue purified via flash column chromatography (silica gel, 0.5-12% EtOH/CH2Cl2) to afford an oil, which was dissolved in a small amount of methylene chloride and to which was then added heptane. A white solid precipitated to afford 110 mg of 2-(4-cyclohexyl-phenoxymethyl)-2,3,5,6-tetrahydro-oxazolo[3,2-a]pyrimidin-7-one.

Workup

customThe solvent was removed under vacuum
customthe residue purified via flash column chromatography (silica gel, 0.5-12% EtOH/CH2Cl2)
customto afford an oil, which
customA white solid precipitated

Sources & evidence

ORD record: ord-625bb452c0c344cea48c956890644473
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642603B2

Reaction notes

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