Ethyl pent-2-yn-1-oate → 2-(4-Cyclohexyl-phenoxymethyl)-5-ethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

HRID 237752Notes

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:26])[C:22]#[C:23][CH2:24][CH3:25]>C(O)C>[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:26])[CH:22]=[C:23]([CH2:24][CH3:25])[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: 170 °C

Procedure

To a solution of 5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine (300 mg, 1.095 mmol) in ethanol (6 mL) was added ethyl 2-pentynoate (276 mg, 2.19 mmol). The reaction mixture was heated in a microwave oven at 170° C. for 70 min. The solvent was removed under vacuum, and the residue purified via flash column chromatography (silica gel, 1-12% EtOH/CH2Cl2) to afford 153 mg of 2-(4-cyclohexyl-phenoxymethyl)-5-ethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one as a slightly yellow solid.

Workup

customThe solvent was removed under vacuum
customthe residue purified via flash column chromatography (silica gel, 1-12% EtOH/CH2Cl2)

Sources & evidence

ORD record: ord-88f53a4b7aa74ec69ca7611dcd838e8c
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642603B2

Reaction notes

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