Nitric Acid → HCID 178503569, Verbindung

HRID 469180

Reaktionsgleichung

Reaktionsgleichung von HRID 469180
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.FC(F)(F)C(O)=O.[N+:18]([O-])([OH:20])=[O:19]>O>[OH:1][C:2]1[C:7]([N+:18]([O-:20])=[O:19])=[C:6]([OH:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 6422Trifluoroacetic acidHCID 178503559HCID 178503559, Verbindung

Produkt 1

HCID 178503569HCID 178503569, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

A solution of 4,6-dihydroxy-2-methylthiopyrimidine (42 g, 0.257 mol) in trifluoroacetic acid (91 ml, 1.186 mol) was stirred at 23° C. and warmed until all solid had gone into solution. The reaction was stirred for five hours at 23° C. Next, fuming HNO3 (15 ml, 350 mmol) was added portion wise to the reaction mixture over 25 minutes at 0° C. The reaction was stirred for twenty hours at 23° C., and treated with H2O (at 23° C.) at 80% conversion (according LC-MS). The solid precipitate was captured via filteration giving 4,6-dihydroxy-2-methylthio-5-nitropyrimidine as a tan-colored solid. The crude solid was azeotroped with toluene to give 35 g of pale tan powdery solid. 1H-NMR: 300 MHz, (CD3OD, 300 MHz) δ (ppm) 2.63 (s, 3H). LCMS-ESI−: calc'd for C5H4N3O4S: 202.0 (M−H−). Found: 202.0 (M−H−).

Aufarbeitung

  1. temperaturewarmed until all solid
  2. stirringThe reaction was stirred for twenty hours at 23° C.

Quellen und Nachweise

ORD-Eintrag
ord-f8c243be74e9489aa155f09977722012
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629142B2

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