Reaktion #470654

Reaktionsgleichung

4,6-dihydroxy-2-methylthiopyrimidine

trifluoroacetic acid

HNO3

→

4,6-dihydroxy-2-methylthio-5-nitropyrimidine

Lösungsmittel

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwarmed until all solid
2. 2
   workup.STIRRINGThe reaction was stirred for twenty hours at 23° C.

Vorschrift

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) d (ppm) 2.63 (s, 3H). LCMS-ESI+: calc'd for C5H4N3O4S: 202.0 (M−H−); Found: 202.0 (M−H−).

Quelle