4-(benzylamino)-5-(hydroxymethyl)pyrimidin-2(1H)-one synthesis

Yield:1333466-54-8 90%

Reaction Conditions:

with triethylamine in water at 60; for 20 h;Reflux;

Steps:

2 Derivatives of 4-N-arylmethylcytosine with hydroxymethylsubstituent at C-5

General procedure: 4-N-Arylmethylcytosine (4, 7) (2.62 mmol, 1 equiv) and paraformaldehyde (180 mg, 6.02 mmol, 2.3 equiv) were added to water (ca. 25 mL) containing triethylamine (2.6 g, 26.00 mmol, 10 equiv). The mixture was refluxed for 8 h and then the flask was closed and kept in oven at 60 C for 12 h. After that the solvents were removed by evaporation under the reduced pressure and ethanol (25 mL) was added to a residue causing to precipitate a white powder. The powder was filtered and dissolved in methanol (0.2e0.5 mL) and again precipitated with ethanol (25 mL). This procedure was repeated two more times 5.1.6.2
4-N-Benzyl-5-hydroxymethylcytosine (16)
Yield 80-90%, 484-545 mg. MS (ESI, pos.) m/z: 232 [M + H]⁺;254 [M + Na]⁺; 270 [M + K]⁺; 485 [2M + Na]⁺. ¹H NMR: δ 4.2 (d, J = 4.8 Hz, 2H, H-15); 4.5 (d, J = 5.7 Hz, 2H, H-8); 7.2-7.3 (m, 5H, Ar); 7.6 (s, 1H, H-6); 10.5 (s, 1H, NH-1).
¹³C NMR (100 MHz, DMSO-d₆): δ 45.48; 57.15; 104.96; 126.82; 127.08; 127.39; 128.18; 128.31; 139.53; 141.70; 156.56; 163.22.

References:

Plitta, Beata;Adamska, Ewelina;Giel-Pietraszuk, Malgorzata;Fedoruk-Wyszomirska, Agnieszka;Naskret-Barciszewska, Miroslawa;Markiewicz, Wojciech T.;Barciszewski, Jan [European Journal of Medicinal Chemistry,2012,vol. 55,p. 243 - 254,12]