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2-(Tributylstannyl)pyridine → 7-(1-azidoethyl)-3-methyl-6-pyridin-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 58244
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 58244
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)CCC.[N:20]([CH:23]([C:25]1[N:26]=[C:27]2[S:35][CH:34]=[C:33]([CH3:36])[N:28]2[C:29](=[O:32])[C:30]=1Br)[CH3:24])=[N+:21]=[N-:22]>O1CCOCC1.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>[N:20]([CH:23]([C:25]1[N:26]=[C:27]2[S:35][CH:34]=[C:33]([CH3:36])[N:28]2[C:29](=[O:32])[C:30]=1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[CH3:24])=[N+:21]=[N-:22]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 6077842-(Tributylstannyl)pyridineHCID 581114387-(1-azidoethyl)-6-bromo-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one

Produkt 1

HCID 866500667-(1-azidoethyl)-3-methyl-6-pyridin-2-yl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneAusbeute 13,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 31275
1,4-Dioxane
Lösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 2-(tributylstannyl)pyridine (Aldrich, 0.176 g, 0.382 mmol), 7-(1-azidoethyl)-6-bromo-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (from example 8, step 3; 0.10 g, 0.318 mmol), and tetrakis(triphenylphosphine)palladium (0) (0.0184 g, 0.0159 mmol) in 1,4-dioxane (0.5 mL) was heated at 65° C. overnight. After being cooled and quenched with saturated ammonium chloride, the resulting mixture was extracted with EtOAc. The organic layers were combined, washed with brine, dried and evaporated to dryness. The residue was purified on silica gel, eluting with 0 to 100% EtOAc in hexane, to provide the desired product (13 mg, 13%). LCMS calculated for C14H13N6OS (M+H)+: m/z=313.1. Found: 313.0.

Aufarbeitung

  1. temperatureAfter being cooled
  2. customquenched with saturated ammonium chloride
  3. extractionthe resulting mixture was extracted with EtOAc
  4. washwashed with brine
  5. customdried
  6. customevaporated to dryness
  7. customThe residue was purified on silica gel
  8. washeluting with 0 to 100% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-30587980d95b4287b0aaa8d0fe257e0e
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09434746B2

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