Boron tribromide → (S)-4-Amino-N-(3,5-dihydroxyphenyl)-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carboxamide

HRID 1052736Notes

Reaction equation

HRID 1052736 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]([O:19]C)[CH:12]=2)=[O:9])=[C:6]([NH:21][C@H:22]([C:24]2[N:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:28](=[O:36])[C:27]3=[C:37]([CH3:40])[CH:38]=[CH:39][N:26]3[N:25]=2)[CH3:23])[N:5]=[CH:4][N:3]=1.B(Br)(Br)Br>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]([OH:19])[CH:12]=2)=[O:9])=[C:6]([NH:21][C@H:22]([C:24]2[N:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:28](=[O:36])[C:27]3=[C:37]([CH3:40])[CH:38]=[CH:39][N:26]3[N:25]=2)[CH3:23])[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 118433938(S)-4-Amino-N-(3,5-dimethoxyphenyl)-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carboxamide

Product 1

HCID 90102389(S)-4-Amino-N-(3,5-dihydroxyphenyl)-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carboxamideYield 3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-4-Amino-N-(3,5-dimethoxyphenyl)-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carboxamide (720 mg, 33% purity, 0.43 mmol) was treated with boron tribromide (1M in dichloromethane, 2.60 ml, 2.6 mmol) in dichloromethane (10 ml) according to the method described in Example 23. The residue was purified by reverse phase using SP1® Purification System to give 36 mg (3% yield) as a solid. Purity 99%.

Workup

  1. customThe residue was purified by reverse phase
  2. custom® Purification System
  3. customto give 36 mg (3% yield) as a solid

Sources & evidence

ORD record
ord-8ce144a4a6f647e79a70801509cac9cb
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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