2-Amino-5-fluoro-4,6-dihydroxypyrimidine

2-Amino-5-fluoro-4,6-dihydroxypyrimidine

 

 

 

Guanidine sulfate (5.95 g, 55 mmol) was added to the solution of sodium (2.50 g, 110 mmol) in anhydrous ethanol (100 mL) and the mixture was heated to reflux. Diethyl 2-fluoromalonate (8.90 g, 50 mmol, 93% pure) was added dropwise over 20 minutes and the mixture was heated at reflux for 6 h. After cooling to room temperature, the solution was evaporated to dryness, the residue was dissolved in water (20 mL), neutralised with HCl to pH 7, the precipitated product was filtered, washed with water (5 mL), ethanol (2 × 5 mL) and diethyl ether (2 × 5 mL). After drying in vacuo, 2-amino-5-fluoro-4,6-dihydroxypyrimidine (6.21 g, 86%) was obtained as a pink powder.

m.p.: >300 °C ([M + H]⁺, 146.0357, C₄H₅FN₃O₂ requires: [M]⁺, 146.0366);

IR (neat,cm⁻¹) 3343, 3100, 2916, 2731, 1600, 1557, 1415, 1358, 1204;  

δ_H (DMSO d₆, 400 MHz) 7.00 (2H, bs, N–H), 11.1 (2H, bs, OH); δ_F (DMSO d₆, 376 MHz): – 197.05 (s);  

δ_C (DMSO d₆, 100 MHz) 125.13 (d, ¹J_CF 208.6, C–F), 149.26 (d, ⁴J_CF 2.3, C–H), 155.12 (d, ²J_CF 18.0, C–OH);  

m/z (ASAP) 146 (100%, [M + H]⁺).
(a) E. D. Bergmann, S. Cohen and I. Dharak, J. Chem. Soc., 1959, 3286–3289
 http://pubs.rsc.org/en/content/articlehtml/2015/gc/c5gc00402k




DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO .....FOR BLOG HOME CLICK HERE

Join me on Linkedin

Join me on Facebook FACEBOOK

Join me on twitter     

Join me on google plus Googleplus

 amcrasto@gmail.com

//