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

HRID 1052442Notes

Reaction equation

HRID 1052442 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[C:15]([O:17]C)[CH:14]=[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]=[C:15]([OH:17])[CH:14]=[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 901032174-Amino-6-chloro-N-(3-fluoro-5-methoxyphenyl)pyrimidine-5-carboxamide

Product 1

HCID 901021654-Amino-6-bromo-N-(3-fluoro-5-hydroxyphenyl)pyrimidine-5-carboxamideYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Amino-6-chloro-N-(3-fluoro-5-methoxyphenyl)pyrimidine-5-carboxamide (458 mg, 1.54 mmol) was treated with boron tribromide (1M in dichloromethane, 0.46 ml, 4.6 mmol) an using dichloromethane (7 ml) as a solvent according to the method described in Example 23. The solid residue (394 mg, 71% yield) was used in the next synthetic step without further purification. Purity 91%.

Sources & evidence

ORD record
ord-7e6e8029d4014d7ea1a6998eb1561b48
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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