Boron tribromide → (S)-2-(1-((6-Amino-5-((3-fluoro-4-hydroxyphenyl)thio)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052718Notes

Reaction equation

HRID 1052718 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1[S:28][C:29]1[CH:34]=[CH:33][C:32]([O:35]C)=[C:31]([F:37])[CH:30]=1.B(Br)(Br)Br>ClCCl>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1[S:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([F:37])[CH:30]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 118433973(S)-2-(1-((6-Amino-5-((3-fluoro-4-methoxyphenyl)thio)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 73775411(S)-2-(1-((6-Amino-5-((3-fluoro-4-hydroxyphenyl)thio)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-(1-((6-Amino-5-((3-fluoro-4-methoxyphenyl)thio)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (233 mg, 0.45 mmol) was treated with boron tribromide (1M in dichloromethane, 1.35 ml, 1.35 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 40 mg (18% yield) as a solid. Purity 99%.

Workup

  1. customThe residue was purified by reverse phase
  2. custom® Purification System
  3. customto give 40 mg (18% yield) as a solid

Sources & evidence

ORD record
ord-63742ffc6d5c4904a62d31cef97659be
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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