Bromine → HCID 90102979, compound

HRID 1052456Notes

Reaction equation

HRID 1052456 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:21][CH:20]=[N:19][CH:18]=3)=[C:13]([O:22]C)[CH:12]=2)=[O:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.B(Br)(Br)[Br:26].BrBr>ClCCl>[NH2:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:21][CH:20]=[N:19][CH:18]=3)=[C:13]([OH:22])[CH:12]=2)=[O:9])=[C:6]([Br:26])[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 25134Boron tribromideHCID 901032614-Amino-6-chloro-N-(3-methoxy-4-(oxazol-5-yl)phenyl)pyrimidine-5-carboxamide

Product 1

HCID 90102979HCID 90102979, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Amino-6-chloro-N-(3-methoxy-4-(oxazol-5-yl)phenyl)pyrimidine-5-carboxamide (788 mg, 1.74 mmol) was treated with boron tribromide (1 M in dichloromethane, 11.8 ml, 11.8 mmol) with dichloromethane (10 ml) as a solvent according to the method described in Example 23. In this reaction conditions the chlorine atom was transformed into bromine. The solid residue (220 mg, 33% yield) was used in the next synthetic step without further purification. Purity 99%.

Workup

  1. customIn this reaction conditions the chlorine atom

Sources & evidence

ORD record
ord-ab69d929f55e488e8701cc35691bb761
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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