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Potassium Phosphate, Tribasic → 7-(1-methyl-1H-pyrazol-4-yl)-5-(1H-pyrrol-3-yl)imidazo[1,2-c]pyrimidine

HRID 1852970
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1852970
Cl[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[C:4]([C:11]2[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=2)[N:3]=1.C([Si](C(C)C)(C(C)C)[N:21]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22]1)(C)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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.O1CCOCC1>[CH3:16][N:14]1[CH:15]=[C:11]([C:4]2[N:3]=[C:2]([C:23]3[CH:24]=[CH:25][NH:21][CH:22]=3)[N:7]3[CH:8]=[CH:9][N:10]=[C:6]3[CH:5]=2)[CH:12]=[N:13]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 27633031-(Triisopropylsilyl)pyrrole-3-boronic acidHCID 86685297HCID 86685297, Verbindung

Produkt 1

HCID 1363877957-(1-methyl-1H-pyrazol-4-yl)-5-(1H-pyrrol-3-yl)imidazo[1,2-c]pyrimidineAusbeute 130 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

To a flask charged with 5-chloro-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (Preparation J; 0.150 g, 0.642 mmol), 1-(triisopropylsilyl)-1H-pyrrol-3-ylboronic acid (0.257 g, 0.963 mmol), and potassium phosphate (0.321 mL, 0.642 mmol) was added 6 mL of dioxane and argon was bubbled through the mixture for 15 minutes. Tetrakis(triphenylphosphine)palladium (0) (0.0742 g, 0.0642 mmol) was added and argon was bubbled through the reaction for 15 minutes. The flask was sealed under argon and the mixture was heated at 75° C. with stirring overnight. The reaction was then concentrated under reduced pressure and then taken up in DCM (5 mL). A precipitate was formed and collected by means of vacuum filtration and washed with DCM (10 mL). The solid contained product without the triisopropylsilyl protection as well as inorganic salts. Further purification was not attempted and so was obtained 7-(1-methyl-1H-pyrazol-4-yl)-5-(1H-pyrrol-3-yl)imidazo[1,2-c]pyrimidine (0.220 g, 0.832 mmol, 130% yield). MS (apci) m/z=265.1 (M+H).

Aufarbeitung

  1. customwas bubbled through the mixture for 15 minutes
  2. customargon was bubbled through the reaction for 15 minutes
  3. customThe flask was sealed under argon
  4. concentrationThe reaction was then concentrated under reduced pressure
  5. customA precipitate was formed
  6. filtrationcollected by means of vacuum filtration
  7. washwashed with DCM (10 mL)
  8. customFurther purification

Quellen und Nachweise

ORD-Eintrag
ord-8e3b15642fca41239338daa4e0c3e114
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08962596B2

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