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

HRID 81382Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:10]=[C:9]([C:11]3[CH:16]=[C:15]([CH3:17])[C:14]([O:18]C)=[C:13]([CH3:20])[CH:12]=3)[O:8][C:6]=2[N:7]=1.B(Br)(Br)Br.[Na]>ClCCl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:10]=[C:9]([C:11]3[CH:12]=[C:13]([CH3:20])[C:14]([OH:18])=[C:15]([CH3:17])[CH:16]=3)[O:8][C:6]=2[N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1.2 g of 5-chloro-2-(4-methoxy-3,5-dimethyl-phenyl)-oxazolo[5,4-d]pyrimidine in 42 ml of dichloromethane was cooled to 0° C., and over a period of 10 min 10 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 3 ml of a 1 M solution of boron tribromide in dichloromethane were added. After stirring for another 1 h, 20 ml of a saturated aqueous solution of sodium hydrogencarboante were added slowly. The precipitate was filtered off and washed with water to give 1 g of the title compound.

Workup

stirringAfter stirring for another 1 h
filtrationThe precipitate was filtered off
washwashed with water

Sources & evidence

ORD record: ord-86e8d823011f4aa8bebe9cec77982dbd
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846692B2

Reaction notes

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