Reference of 31519-62-7 ,Some common heterocyclic compound, 31519-62-7, molecular formula is C5H4N2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
114. f+)-2-f(3.,4-trans)-4-methyl-l-fpyrimi(iine-2-carbonyl)pyrroli(iin-3- yl)-7-ftetrahvdro-2H-pyran-4-yl)imidazo[5,l- 1 [l,2,41triazin-4f3H -one [1073] To a stirred solution of (+)-2-((3,4-trans)-4-methylpyrrolidin-3-yl)-7- (tetrahydro-2H-pyran-4-yl)imidazo[5,l: ][l,2,4]triazin-4(3H)-one (75 mg, 0.24 mmol) in DMF (5 mL) were added EDCI (70 mg, 0.37 mmol), HOBt (50 mg, 0.37 mmol), DIPEA (95 mg, 0.74 mmol) and pyrimidine-2-carboxylic acid (40 mg, 0.32 mmol) at 0 C under inert atmosphere. The resulting reaction mixture was allowed to warm to room temperature and stirred for 8 h. The reaction mass was diluted with water (100 mL) and extracted with DCM (3 x 50 mL). Combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was purified by silica gel column chromatography to afford (+)-2-((3,4-trans)-4-methyl-l-(pyrimidine-2-carbonyl)pyrrolidin-3-yl)-7- (tetrahydro-2H-pyran-4-yl)imidazo[5,l: ][l,2,4]triazin-4(3H)-one (40 mg, 40%) as an off-white solid. 1H-NMR (DMSO d6, 400 MHz): delta 11.95 (bs, 1H), 8.97 (d, 2H), 6.69- 6.58 (m, 2H), 3.98-3.84 (m, 4H), 3.65-3.57 (m, 4H), 3.22-3.27 (m, 2H), 2.68-2.61 (m, 1H), 1.90-1.84 (m, 4H), 1.08 (d, 3H); Mass (ESI): 410 [M++l] LC-MS: 98.92%; 410.3 (M++l); (column; X-bridge C-18, (50×3.0 mm, 3.5mu); RT 1.85 min. 0.05% TFA in water: ACN; 0.8 ml/min); UPLC (purity): 98.76%; (column; Eclipse XDB C- 18, (150×4.6 mm, 5.0mu); RT 8.23 min. 5mM NH4OAc (Aq): ACN; 1.0 ml/min; Chiral HPLC: 99%, R, = 37.69 min (Chiralpak IA, 250 x 4.6mm, 5mu; mobile phase (A) n- Hexane (B) DCM:MeOH (80:20) (A: B : 80:20); flow Rate: 1.00 mL/min); Optical rotation [a]D2: +12.17 (c = 0.25, DCM). TLC: 10% MeOH/DCM (Rf: 0.5).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 31519-62-7, 2-Pyrimidinecarboxylic acid, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia