Boron tribromide → 2-(4-(4-Chloro-2-hydroxyphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoic acid

HRID 1399678Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14]([CH2:19][CH2:20][CH3:21])[C:15]([O:17]C)=[O:16])=[C:12]([CH3:22])[N:11]=[C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:9]=2)=[C:4]([O:29]C)[CH:3]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14]([CH2:19][CH2:20][CH3:21])[C:15]([OH:17])=[O:16])=[C:12]([CH3:22])[N:11]=[C:10]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:9]=2)=[C:4]([OH:29])[CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a cooled (−78° C.) stirred solution of methyl 2-(4-(4-chloro-2-methoxyphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (0.125 mg; 0.294 mmol) in dichloromethane (1.5 mL) was added a solution of boron tribromide (1M in dichloromethane) (0.340 mL; 0.340 mmol) dropwise. After 1 h the mixture was allowed to warm up to room temperature and the reaction was stirred for 16 h. The reaction was quenched by adding water and the mixture was extracted with ethyl acetate, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purifications by flash-chromatography on silica gel using a gradient of methanol (0-10%) in dichloromethane and by preparative TLC on silica gel using a mixture methanol-dichloromethane (5:95) as eluent furnished 0.0018 g (1.5%) of the title compound.

Workup

temperatureto warm up to room temperature
customThe reaction was quenched
additionby adding water
extractionthe mixture was extracted with ethyl acetate
dry with materialdried over magnesium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-9b0e704a2bda4f18b6e7bd9aa8e13230
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906906B2

Reaction notes

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