Boron tribromide → (S)-4-Amino-6-((1-(5-((3-hydroxyphenyl)thio)-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carbonitrile

HRID 1052659Notes

Reaction equation

HRID 1052659 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C@H:11]([C:13]2[N:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:17](=[O:25])[C:16]3=[C:26]([S:29][C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([O:36]C)[CH:31]=4)[CH:27]=[CH:28][N:15]3[N:14]=2)[CH3:12])[N:5]=[CH:4][N:3]=1.B(Br)(Br)Br>ClCCl>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C@H:11]([C:13]2[N:18]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:17](=[O:25])[C:16]3=[C:26]([S:29][C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([OH:36])[CH:31]=4)[CH:27]=[CH:28][N:15]3[N:14]=2)[CH3:12])[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 118433760(S)-4-Amino-6-((1-(5-((3-methoxyphenyl)thio)-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carbonitrile

Product 1

HCID 73774947(S)-4-Amino-6-((1-(5-((3-hydroxyphenyl)thio)-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carbonitrileYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-4-Amino-6-((1-(5-((3-methoxyphenyl)thio)-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidine-5-carbonitrile (70 mg, 0.14 mmol) was treated with boron tribromide (1M in dichloromethane, 411 μl, 0.41 mmol) with dichloromethane as a solvent according to the method described in Example 23. The residue was purified by reverse phase using SP1® Purification System to give 33 mg (49% yield) as a solid. Purity 100%.

Workup

  1. customThe residue was purified by reverse phase
  2. custom® Purification System
  3. customto give 33 mg (49% yield) as a solid

Sources & evidence

ORD record
ord-fa540f24b7ff4ffebaf038deef2b0bc7
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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