Boron tribromide → 4-[5-(2-Fluorophenoxy)oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenol

HRID 81360Notes

Reaction equation

[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[O:4][C:5]1[N:6]=[CH:7][C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[C:17]([O:21]C)=[C:16]([CH3:23])[CH:15]=3)[O:11][C:9]=2[N:10]=1.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[O:4][C:5]1[N:6]=[CH:7][C:8]2[N:13]=[C:12]([C:14]3[CH:15]=[C:16]([CH3:23])[C:17]([OH:21])=[C:18]([CH3:20])[CH:19]=3)[O:11][C:9]=2[N:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 510 mg of 5-(2-fluoro-phenoxy)-2-(4-methoxy-3,5-dimethyl-phenyl)-oxazolo[5,4-d]pyrimidine in 20 ml dichloromethane was cooled to 0° C., and over a period of 10 min 4.2 ml of a 1 M solution of boron tribromide in dichloromethane was added. The mixture was stirred at 0° C. for 1 h, and then another 2 ml of a 1 M solution of boron tribromide in dichloromethane were added. After stirring for another 1 h, 10 ml of a saturated aqueous solution of sodium hydrogencarbonate were added slowly. The aqueous layer was extracted twice with 15 ml of dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and the solvents were removed in vacuo to give 445 mg of the title compound as a white solid.

Workup

stirringAfter stirring for another 1 h
extractionThe aqueous layer was extracted twice with 15 ml of dichloromethane
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
customthe solvents were removed in vacuo

Sources & evidence

ORD record: ord-3e806db210bc4a969dbe8d525952d1e4
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846690B2

Reaction notes

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