Category: 55150-17-9

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 55150-17-9, name is 4-Ethoxypyrimidin-5-amine, molecular formula is C6H9N3O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. COA of Formula: C6H9N3O

To a solution of 2-phenylimidazo[l,2-Z>]pyridazine-8-carboxylic acid (40 mg, 0.167 mmol) and 4-ethoxypyrimidin-5 -amine (46.5 mg, 0.334 mmol) in DMF (2 mL) was added N,N-diisopropylethylamine (0.175 mL, 1.003 mmol) and HATU (127 mg, 0.334 mmol). The reaction mixture was stirred at rt for 2 h. The reaction mixture was transferred to a separatory funnel containing saturated aqueous NaHCCb solution (15 mL). The aqueous layer was extracted with ethyl acetate (3 x 15 mL). The combined organic layers were washed with brine (20 mL), dried over MgS04, filtered, and concentrated. The residue was purified by column chromatography on silica gel (80%? 90% ethyl acetate in hexanes; 24 g column) to afford N-(4-ethoxypyrimidin-5-yl)-2- phenylimidazo[l,2-)]pyridazine-8-carboxarnide (20 mg, 0.055 mmol, 33% yield) as a yellow solid: NMR (400MHz, DMSO-de) delta 12.28 (s, IH), 9.64 (s, IH), 9.17 (s, IH), 8.81 (d, J=4.8 Hz, IH), 8.65 (s, IH), 8.27 – 8.23 (m, 2H), 7.92 (d, J=4.8 Hz, IH), 7.60 – 7.55 (m, 2H), 7.50 – 7.45 (m, IH), 4.79 (q, J=7.0 Hz, 2H), 1.47 (t, J=7.0 Hz, 3H); LCMS (ESI) m/e 361.1 [(M+H) + , calcd for CioHnNeC 361.1]; HPLC (Method A): fe. = 13.50 min; (Method B) = 12.55 min.

With the rapid development of chemical substances, we look forward to future research findings about 55150-17-9.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARTZ, Richard A.; AHUJA, Vijay T.; SIVAPRAKASAM, Prasanna; DUBOWCHIK, Gene M.; MACOR, John E.; (104 pag.)WO2018/98411; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 55150-17-9 ,Some common heterocyclic compound, 55150-17-9, molecular formula is C6H9N3O, 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.

(2) 2,2,2-Trichloroethyl (4-ethoxyprimidin-5-yl)carbamate; To a solution of 4-ethoxypyrimidine-5-amine (1.00 g, 7.19 mmol) and pyridine (1.74 ml, 21.6 mmol) in tetrahydrofuran (20 ml) was added 2,2,2-trichloroethyl chloroformate (1.49 ml, 10.8 mmol) with ice-cooling, the mixture was stirred for 30 minutes with ice-cooling, the reaction mixture was poured into ice-water and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of ethyl acetate and hexane to obtain the desired product (1.73 g, 76.5%) as a solid. 1H-NMR (CDCl3) delta; 1.48 (3H, t, J = 7.2 Hz), 4.55 (2H, q, J = 7.2 Hz), 4.87 (2H, s), 7.15(1H, br s), 8.51 (1H, s), 9.20 (1H, br s).

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. 55150-17-9, 4-Ethoxypyrimidin-5-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1813606; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia