6-Benzyloxy-5-nitroso-pyrimidine-2,4-diamine synthesis

Yield:101724-61-2 98%

Reaction Conditions:

with acetic acid;sodium nitrite in water at 80; for 1 h;

Steps:

2,6-Diamino-4-benzyloxypyrimidine (0.5 g, 2.3 mmol) was dissolved in warm acetic acid (30%, 10 ml) and the reaction mixture was heated to 80° C. A solution of sodium nitrite (0.22 g, 3.19 mmol) in water (5 ml) was added dropwise over 1 h, when an excess of oxidant was evident by starch-iodide paper. The reaction mixture was allowed to cool to room temperature, and the violet crystals which deposited were collected and washed with water (0.53 g, 98%), m.p. decomposed 209° C.; (Found: C, 55.32; H, 5.28; N, 26.47% C₁₁H₁₁N₅O₂ 0.1 H₂O C, 55.98; H, 4.75; N, 29.69%); ν_max/cm^-1 3408 (NH), 2952 (CH₂), 1610 (C₆H₅), 1518 (NO); δ_H (200 MHz, d₆-DMSO) 5.69 (2H, s, OCH₂), 7.44-7.68 (5H, m, C₆H₅), 8.0 (2H, d, NH₂), 8.17 (1H, s, NH) , 10.19 (1H, s, NH); m/z (+EI) 245 (M₊, 25%), 91 (100), 65 (9).

References:

US6677345,2004,B1 Location in patent:Page/Page column 11