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

HRID 1052858Notes

Reaction equation

HRID 1052858 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([NH:16][C:17]([NH2:19])=[O:18])[CH:11]=[C:12]([O:14]C)[CH:13]=2)=[C:6]([NH:20][C@H:21]([C:23]2[N:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:27](=[O:35])[C:26]3=[C:36]([CH3:39])[CH:37]=[CH:38][N:25]3[N:24]=2)[CH3:22])[N:5]=[CH:4][N:3]=1.B(Br)(Br)Br>ClCCl>[NH2:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([NH:16][C:17]([NH2:19])=[O:18])[CH:11]=[C:12]([OH:14])[CH:13]=2)=[C:6]([NH:20][C@H:21]([C:23]2[N:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:27](=[O:35])[C:26]3=[C:36]([CH3:39])[CH:37]=[CH:38][N:25]3[N:24]=2)[CH3:22])[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 90102996(S)-1-(3-(4-Amino-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)-5-methoxyphenyl)urea

Product 1

HCID 90102985(S)-1-(3-(4-Amino-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)-5-hydroxyphenyl)ureaYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-1-(3-(4-Amino-6-((1-(5-methyl-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)ethyl)amino)pyrimidin-5-yl)-5-methoxyphenyl)urea (50 mg, 0.10 mmol) was dissolved in dichloromethane (1.5 ml). A solution of boron tribromide (1M in dichloromethane, 285 μl, 0.29 mmol) was added dropwise and the reaction was stirred at room temperature overnight. The mixture was diluted with dichloromethane and washed with a solution of 4% sodium bicarbonate, water, brine and dried over sodium sulphate, filtered and evaporated under reduced pressure. The product was purified by reverse phase using SP1® Purification System to give 27 mg (55% yield) of the title compound. Purity 100%.

Workup

  1. washwashed with a solution of 4% sodium bicarbonate, water, brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe product was purified by reverse phase
  6. custom® Purification System

Sources & evidence

ORD record
ord-f166c93910f743f283d0f7a4f014782a
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

Loading…