Boron tribromide → (S)-4-Amino-N-(3-hydroxybenzyl)-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 1052727Notes

Reaction equation

HRID 1052727 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18]C)[CH:13]=2)=[O:9])=[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]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)=[O:9])=[C:6]([NH:20][C@H:21]([C:23]2[N:28]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=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 118433935HCID 118433935, compound

Product 1

HCID 73775679(S)-4-Amino-N-(3-hydroxybenzyl)-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 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-4-Amino-N-(3-methoxybenzyl)-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 (103 mg, 0.20 mmol) was treated with boron tribromide (1M in dichloromethane, 0.85 ml, 0.85 mmol) in dichloromethane (8 ml) according to the method described in Example 23. The residue was purified by reverse phase using SP1® Purification System to give 37 mg (36% yield) as a solid. Purity 98%.

Workup

  1. customThe residue was purified by reverse phase
  2. custom® Purification System
  3. customto give 37 mg (36% yield) as a solid

Sources & evidence

ORD record
ord-15879f581ea9440f88c20591c27fedb2
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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