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

HRID 1027713Notes

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.C(=O)(O)[O-].[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-dimethylphenyl)oxazolo[5,4-d]pyrimidine in 42 ml of dichloromethane was cooled to 0° C., and 10 ml of a 1 M solution of boron tribromide in dichloromethane were added over a period of 10 min. The mixture was stirred at 0° C. for 1 h, and a further 3 ml of a 1 M solution of boron tribromide in dichloromethane were then added. After another hour of stirring, 20 ml of saturated aqueous sodium bicarbonate solution were added slowly. The precipitate was filtered off and washed with water, which gave 1 g of the title compound.

Workup

stirringAfter another hour of stirring
filtrationThe precipitate was filtered off
washwashed with water, which

Sources & evidence

ORD record: ord-495f2da19e164332829d779c679c3f6a
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735402B2

Reaction notes

Loading…