Boron tribromide → 4-Amino-6-bromo-N-(3-fluoro-4-hydroxyphenyl)pyrimidine-5-carboxamide

HRID 1052439Notes

Reaction equation

HRID 1052439 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17]C)=[C:13]([F:19])[CH:12]=2)=[O:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.B(Br)(Br)[Br:22]>ClCCl>[NH2:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([F:19])[CH:12]=2)=[O:9])=[C:6]([Br:22])[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 901026694-Amino-6-chloro-N-(3-fluoro-4-methoxyphenyl)pyrimidine-5-carboxamide

Product 1

HCID 901033674-Amino-6-bromo-N-(3-fluoro-4-hydroxyphenyl)pyrimidine-5-carboxamideYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Amino-6-chloro-N-(3-fluoro-4-methoxyphenyl)pyrimidine-5-carboxamide (675 mg, 2.28 mmol) was treated with boron tribromide (1M in dichloromethane, 6.80 ml, 6.80 mmol) and using dichloromethane (10 ml) as a solvent according to the method described in Example 23. The solid residue (280 mg, 38% yield) was used in the next synthetic step without further purification. Purity 99%.

Sources & evidence

ORD record
ord-587d8aace5cd446c9f96a68df5d28e63
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

Loading…