Hydrogen Peroxide → 5-Pyrimidinecarboxamide, 2-[(1-methylcyclopropyl)amino]-4-(methylthio)-

HRID 2280799Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2280799
[CH3:1][C:2]1([NH:5][C:6]2[N:11]=[C:10]([S:12][CH3:13])[C:9]([C:14]#[N:15])=[CH:8][N:7]=2)[CH2:4][CH2:3]1.[OH-:16].[Na+].OO>CS(C)=O.C(OCC)(=O)C.O>[CH3:1][C:2]1([NH:5][C:6]2[N:11]=[C:10]([S:12][CH3:13])[C:9]([C:14]([NH2:15])=[O:16])=[CH:8][N:7]=2)[CH2:4][CH2:3]1

Komponenten

7

Edukt 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 71237560HCID 71237560, Verbindung

Produkt 1

HCID 712371065-Pyrimidinecarboxamide, 2-[(1-methylcyclopropyl)amino]-4-(methylthio)-Ausbeute 43,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a stirring solution of 2-(1-methylcyclopropylamino)-4-(methylthio)pyrimidine-5-carbonitrile (0.653 g, 2.96 mmol, synthesis described herein) in DMSO (8 mL) was added 6N aqueous sodium hydroxide (2.470 mL, 14.82 mmol) solution and 30% aqueous hydrogen peroxide solution (1.873 mL, 16.52 mmol) at 0° C. Then the mixture was stirred at 50° C. and for 20 minutes and was then diluted with 100 mL ethyl acetate and 30 mL water. The layers were separated and the aqueous layer was back extracted with 50 mL ethyl acetate. The combined ethyl acetate layers were dried over anhydrous magnesium sulfate, filtered and concentrated to solids that were dried in a vacuum oven at 45° C. to afford 2-(1-methylcyclopropylamino)-4-(methylthio)pyrimidine-5-carboxamide (305 mg, 1.280 mmol, 43.2% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.31-8.54 (m, 1H), 7.80-8.07 (m, 1H), 6.97-7.77 (m, 1H), 2.39 (br. s., 3H), 1.37 (s, 3H), 0.52-0.79 (m, 4H). MS (ESI) m/z 239.0 [M+1]+.

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe aqueous layer was back extracted with 50 mL ethyl acetate
  3. dry with materialThe combined ethyl acetate layers were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to solids that
  6. customwere dried in a vacuum oven at 45° C.

Quellen und Nachweise

ORD-Eintrag
ord-80d5b2de66ba4616b88a7bc9ba697bff
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139534B2

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