Phenol → Methyl 2-(4-methyl-6-phenoxy-2-phenylpyrimidin-5-yl)pentanoate

HRID 1399644Notes

Reaction equation

[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:15]1[C:20]([CH:21]([CH2:26][CH2:27][CH3:28])[C:22]([O:24][CH3:25])=[O:23])=[C:19]([CH3:29])[N:18]=[C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:16]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[CH3:29][C:19]1[C:20]([CH:21]([CH2:26][CH2:27][CH3:28])[C:22]([O:24][CH3:25])=[O:23])=[C:15]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:16]=[C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Phenol (0.141 g; 1.5 mmol) and cesium carbonate (0.489 g; 1.5 mmol) were added to a solution of methyl 2-(4-chloro-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (0.159 g; 0.5 mmol) in tetrahydrofuran (1.5 mL) and heated in a seal tube to 100° C. for 18 h. The mixture was diluted with a saturated solution of sodium hydrogen carbonate and was extracted with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-40%) in heptane furnished 0.129 g (58%) of the title compound.

Workup

extractionwas extracted with ethyl acetate
washThe combined organics were washed with brine
dry with materialdried over magnesium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure
customPurification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-40%) in heptane

Sources & evidence

ORD record: ord-4b930a33b41844bf9f4c291cf586b28c
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906906B2

Reaction notes

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