4-(2-Fluoropropan-2-yl)pyrimidine-5-carbonitrile → HCID 82417295, Verbindung

HRID 1749415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749415
F[C:2]([C:5]1[C:10]([C:11]#[N:12])=[CH:9][N:8]=[CH:7][N:6]=1)([CH3:4])[CH3:3]>C1COCC1.[Ni]>[CH:2]([C:5]1[C:10]([CH2:11][NH2:12])=[CH:9][N:8]=[CH:7][N:6]=1)([CH3:4])[CH3:3]

Komponenten

4

Edukt 1

HCID 726991554-(2-Fluoropropan-2-yl)pyrimidine-5-carbonitrile

Produkt 1

HCID 82417295HCID 82417295, VerbindungAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 4-(2-fluoropropan-2-yl)pyrimidine-5-carbonitrile (1.0 equiv.) and Raney-nickel in THF (0.5 M) was degassed under vacuum. The resulting mixture was hydrogenated under a fully-inflated balloon at room temperature overnight. The mixture was filtered through a pad of celite and the cake was rinsed with MeOH. The filtrate was concentrated and further dried to give a brown oil, which was purified by silica gel column chromatography (0-20% MeOH in ethyl acetate, 50 g column) to give (30% yield) of pale yellow oil as a 3:2 mixture of the above two products. MS (ESI) m/z 152.0 [M+1]+. MS (ESI) m/z 170.0 [M+1]+.

Aufarbeitung

  1. customwas degassed under vacuum
  2. filtrationThe mixture was filtered through a pad of celite
  3. washthe cake was rinsed with MeOH
  4. concentrationThe filtrate was concentrated
  5. customfurther dried
  6. customto give a brown oil, which
  7. customwas purified by silica gel column chromatography (0-20% MeOH in ethyl acetate, 50 g column)

Quellen und Nachweise

ORD-Eintrag
ord-0cd64cc10eec491793f7c67711590c11
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156798B2

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