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3-Butyn-1-OL → 4-(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)but-3-yn-1-ol

HRID 578752
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 578752
Br[C:2]1[N:10]2[C:5]([C:6]([NH2:11])=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.N1CCCC1.[CH2:17]([OH:21])[CH2:18][C:19]#[CH:20]>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[NH4+]>[NH2:11][C:6]1[C:5]2=[CH:4][CH:3]=[C:2]([C:20]#[C:19][CH2:18][CH2:17][OH:21])[N:10]2[N:9]=[CH:8][N:7]=1
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Komponenten

7

Edukt 3

HCID 135663-Butyn-1-OLHCID 31268PyrrolidineHCID 422813837-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine

Produkt 1

HCID 585295674-(4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)but-3-yn-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator
HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (1.0 g, 4.69 mmol), copper(I) iodide (89 mg, 0.47 mmol, 0.1 eq.) and tetrakis(triphenylphosphine)palladium(0) (542 mg, 0.47 mmol, 0.1 eq.) were charged into a microwave reactor vial and evacuated for 1 h. The vessel was then vented with argon, pyrrolidine (15 mL) and 3-butyn-1-ol (3.36 g, 47 mmol, 10 eq.) were added, and the vessel was crimp-capped and heated to 85° C. for 120 min in a single-mode microwave device. After cooling, the reaction mixture was poured into 120 mL of concentrated aqueous ammonium chloride solution and extracted twice with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and evaporated, and the residue was purified by flash chromatography (Biotage silica column, ethyl acetate). The resulting product (735 mg) was sufficiently pure (66% by HPLC) for further transformations.

Aufarbeitung

  1. customevacuated for 1 h
  2. additionwere added
  3. customthe vessel was crimp-capped
  4. temperatureAfter cooling
  5. extractionextracted twice with ethyl acetate
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. customevaporated
  8. customthe residue was purified by flash chromatography (Biotage silica column, ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-ffd49be93791436989cec50e048dfc1b
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09040691B2

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