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

HRID 576912Notes

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 of dichloromethane was cooled to 0° C. 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, and the combined organic layers were dried over sodium sulfate, filtered. The solvents were removed in vacuo to give 445 mg of the title compound as a white solid. LC/MS (method LC2): Rt=3.62 min; m/z=352.13 [M+H]+

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-fbcc6ef97e944388a553ebab3aaff62d
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040544B2

Reaction notes

Loading…