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

HRID 1052670
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1052670
[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[C:28]1[CH:33]=[C:32]([O:34]C)[C:31]([F:36])=[C:30]([F:37])[CH:29]=1.B(Br)(Br)Br>ClCCl.C(OCC)(=O)C>[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:18]=[CH:19][CH:20]=[CH:21][CH:22]=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[C:28]1[CH:33]=[C:32]([OH:34])[C:31]([F:36])=[C:30]([F:37])[CH:29]=1
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Komponenten

5

Edukt 2

HCID 25134Boron tribromideHCID 118433822(S)-2-(1-((6-Amino-5-(3,4-difluoro-5-methoxyphenyl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Produkt 1

HCID 73774795(S)-2-(1-((6-Amino-5-(3,4-difluoro-5-hydroxyphenyl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(S)-2-(1-((6-Amino-5-(3,4-difluoro-5-methoxyphenyl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (87 mg, 0.17 mmol) was dissolved in 3 mL dichloromethane. A solution of boron tribromide (1M, 520 μl, 0.52 mmol) was added dropwise and the reaction was stirred at room temperature overnight. Further tribromide (1M in dichloromethane, 260 μl, 0.26 mmol) was added dropwise and stirred for 2 h more. The mixture was diluted with ethyl acetate and washed with a solution of 4% sodium bicarbonate, water, brine and dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified by reverse phase using SP1® Purification System to give 25 mg (44% yield) of the title compound as a solid. Purity 99%.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-fff7f02ca3ca4306bd8a34751b568386
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09388189B2

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