1,1'-Carbonyldiimidazole → 1-methyl-1H,4H,5H,6H,7H-pyrazolo(4,3-d)pyrimidine-5,7-dione

HRID 72180

Reaktionsgleichung

Reaktionsgleichung von HRID 72180
[CH3:1][N:2]1[C:6]([C:7]([NH2:9])=[O:8])=[C:5]([N+:10]([O-])=O)[CH:4]=[N:3]1.C1N=CN([C:18](N2C=NC=C2)=[O:19])C=1>C(#N)C>[CH3:1][N:2]1[C:6]2[C:7](=[O:8])[NH:9][C:18](=[O:19])[NH:10][C:5]=2[CH:4]=[N:3]1

Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 18787291-methyl-4-nitro-1H-pyrazole-5-carboxamide

Produkt 1

HCID 99422421-methyl-1H,4H,5H,6H,7H-pyrazolo(4,3-d)pyrimidine-5,7-dioneAusbeute 91,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

This compound was prepared following the method described in WO2008/071650. To a stirred solution of 1-methyl-4-nitro-1H-pyrazole-5-carboxamide (1.27 g, 9.06 mmol) in acetonitrile (35.6 mL) refluxed at 100° C. was added N,N-carbonyldimidazole (1.91 g, 11.78 mmol, 1.3 eq.) proportion wise over 1 hour. The reaction mixture was stirred at 100° C. under N2 for 18 hours. The resultant precipitate was filtered, rinsed well with cold acetonitrile, and pumped dry on high-vac to yield 1.38 g (91.5%) of a white solid. 1H NMR (DMSO-d6, 500 MHz) δ ppm 11.04 (broad d, 2H), 7.34 (s, 1H), 4.04 (s, 3H).

Aufarbeitung

  1. customThis compound was prepared
  2. filtrationThe resultant precipitate was filtered
  3. washrinsed well with cold acetonitrile
  4. custompumped dry on high-vac

Quellen und Nachweise

ORD-Eintrag
ord-5f2cdd26af564967a8096d121173fb01
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828990B2

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