Synthetic Route of 65996-58-9, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.65996-58-9, name is 2-Amino-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one, molecular formula is C6H6N4O, molecular weight is 150.14, as common compound, the synthetic route is as follows.
To a suspension of 2-amino-SH-pyrrolo [3, [2-D] PYRIMIDIN-4 (3H)-ONE] (9- deazaguanine) (0.454 g, 3.0 mmol) (prepared according to J. Org. Chem. 1978,43, 2536) and 2-O-methyl-1, 3, [5-TRI-O-BENZOYL-D-D-RIBOFURANOSE] (1.54 g, 3.2 mmol) in dry nitromethane (23 mL) at [60C] was added stannic chloride (0.54 mL, 4.5 mmol). The reaction mixture was maintained at this temperature for 0.5 hr. , cooled and poured onto ice-cold saturated sodium bicarbonate solution (70 mL). The insoluble material was filtered through florisil and washed with ethyl acetate [(3X50] mL). The filtrate was extracted with ethyl acetate [(2X50] mL), and organic layer was washed with water [(2X50] mL), dried over [NA2SO4] and evaporated to dryness. Chromatography of the resulting foam on silica gel with [CH2CI2/MEOH] (14: 1) afforded the benzoylated product (0.419 g, 30% yield). To a suspension of the benzoylated product (0.25 g) in MeOH (2.4 mL) was added t-butylamine (0.52 [ML)] and stirring at room temperature was continued for 24 hrs. followed by addition of more t-butylamine [(0. 2] mL). The reaction mixture was stirred at ambient temperature overnight, concentrated in vacuum and the residue was purified by flash chromatography over silica gel using CH2Cl2/MeOH (85: 15) as eluent giving the desired compound as a foam (0.80 g). ‘H NMR [(200MHZ,] [DMSO-D6)] : [3] Hz3.28 (s, 3H), 3.40-3. 52 (m, 3H), 3.87-3. 90 (m, 1H), 4.08-4. 09 (m, 1H), 4.67 (d, 1H, J = 5.2 Hz), 4.74 (d, 1H, J = 7.0 Hz), 5.62 and 5.50 (2 bs, 3H), 7.14 (d, 1H, [J=] 2.6 Hz), 10.43 (s, [LH),] 11.38 (s, [LH)] ; Mass spectrum: calcd. for C12H16N4O5: 296. 28; found: 295.11.
The chemical industry reduces the impact on the environment during synthesis 65996-58-9, I believe this compound will play a more active role in future production and life.
Reference:
Patent; ISIS PHARMACEUTICALS, INC.; WO2003/99840; (2003); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia