Category: 171178-47-5

Synthetic Route of 171178-47-5, 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.171178-47-5, name is 6-Chloropyrido[3,4-d]pyrimidin-4(3H)-one, molecular formula is C7H4ClN3O, molecular weight is 181.58, as common compound, the synthetic route is as follows.

Step (F) : 4- (6-CHLORO-4-OXO-4H-PYRIDO [3,4-d] pyrimidin-3-ylmethyl)-benzoic acid tert-butyl ester A suspension of 6-chloro-3H-pyrido [3,4-d] PYRIMIDIN-4-ONE in DMF (230mL) was treated with cesium carbonate and stirred at room temperature for 1 hour. The mixture was treated with 4-aminomethylbenzoic acid tert-butyl ester (62.2g, 195mmol, 0. 85 mole equivalents) and reaction mixture solidified almost immediately; an additional 100mL of DMF was added. The reaction mixture was stirred at room temperature for 2 hours, heated overnight at 60C, and cooled to room temperature. The mixture was filtered to remove the cesium carbonate, and the filtercake was washed with DMF. Upon standing, a white solid began to form in the filtrate. This solid was collected by filtration, washed with DMF, and then ethyl acetate. The filtrate was evaporated to dryness, and the resulting SOLID/OIL mixture was treated with ethyl acetate and IN HCI, giving two layers. The layers were separated, and the organic portion was evaporated to dryness. The residue was triturated with hot HEXANES/ETHYL acetate 3: 1 and cooled to room temperature. The resulting solid was collected by filtration and washed with hexanes/ethyl acetate 3: 1. The initial white solid from the cesium carbonate wash was combined with this solid, and the combined material was triturated with hot HEXANES/ETHYL acetate 3: 1, cooled to room temperature, and further cooled in a refrigerator for 45 minutes. The solids were collected by filtration, washed with hexanes/ethyl acetate 4: 1, and dried to give 46.32g of 4- (6-chloro-4-oxo-4H-pyrido [3,4- D] PYRIMIDIN-3-YLMETHYL)-BENZOIC acid tert-butyl ester as a light yellow solid (89.5% yield). 1H NMR (400 MHz, DMSO-D6) 8 ppm 1.5 (s, 9H), 3.9 (s, 3H), 5.3 (s, 2H), 7.5 (d, J=8. 5HZ, 2H), 7.8 (d, J=8. 5HZ, 2H), 8.5 (s, 1H), 8.8 (s, 1H), 9.1 (s, 1H) MS (APCI) M+1 = 372.1

The chemical industry reduces the impact on the environment during synthesis 171178-47-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2005/16926; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 171178-47-5 ,Some common heterocyclic compound, 171178-47-5, molecular formula is C7H4ClN3O, 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.

General procedure: A mixture of K2CO3 (267mg, 1.94mmol) and 1 (250mg, 0.969mmol) in anhydrous DMF (5.0mL) was stirred at room temperature for 30min. To this white suspension was added 2a (392mg, 1.94mmol), and the resulting reaction mixture was stirred at room temperature for 2h. The resulting mixture was quenched with water, and the aqueous solution was extracted with EtOAc (3×10.0mL). The combined organic layers were washed with brine (3×10.0mL), dried with anhydrous Na2SO4, filtered, and concentrated under vacuum to give the crude product. The crude product was purified by flash silica gel column chromatography (hexane/CH2Cl2=1/2) to afford 3a as white crystals (276mg, 75%).

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. 171178-47-5, 6-Chloropyrido[3,4-d]pyrimidin-4(3H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Guo, Junsong; Chen, Bingyi; Yu, Ying; Cheng, Bao; Cheng, Yanfang; Ju, Yingchen; Gu, Qiong; Xu, Jun; Zhou, Huihao; European Journal of Medicinal Chemistry; vol. 187; (2020);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 171178-47-5, 6-Chloropyrido[3,4-d]pyrimidin-4(3H)-one, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, COA of Formula: C7H4ClN3O, blongs to pyrimidines compound. COA of Formula: C7H4ClN3O

Step (F) : 4- (6-CHLORO-4-OXO-4H-PYRIDO [3, 4-D] PYRIMIDIN-3-YLMETHYL)-BENZOIC acid tert-butyl ester A 2 L round bottomed flask was charged with 6-chloro-3H-pyrido [3,4- D] PYRIMIDIN-4-ONE (61.9 g, 0.34 moles), CS2CO3 (155 g, 0. 48 moles, 1.4 mole equivalents), and 900 mL of DMF. The slurry was stirred for 5 minutes, then t- butyl-4-bromomethylbenzoate (129 g, 0.48 moles, 1.4 mole equivalents) was added, and stirring of the resulting thick slurry was continued. After 15 minutes HPLC (C18,4 : 1/CH3CN : 0. 1% TFA, 254 nm, 1 ML/MIN) showed less than 3% of 6-chloro-3H-pyrido [3,4-d] PYRIMIDIN-4-ONE remained. After 30 minutes the reaction was complete. Added 450 mL of H20 to the slurry, and collected the resulting solid by filtration. The solid was washed twice with 2: 1/DMF: H20, once with H2O, and dried overnight in the vacuum oven at 45C. The reaction yielded 124 g (98% total) OF 4- (6-CHLORO-4-OXO-4H-PYRIDO [3,4-d] pyrimidin-3- ylmethyl) -benzoic acid tert-butyl ester as a white solid that was 99% pure by HPLC. OH (DMSO) 8.94 (1 H, d), 8. 71 (1 H, s), 7.99 (1 H, d), 7. 83 (2 H, d), 7.45 (2 H, d), 5.26 (2 H, s), 1.49 (9 H, s) MS [M+H] + 372 HPLC 99.02%, RT 2. 90 min ; YMC Pack Pro C18 4. 6X150 mm, 3F ; A: 0.05% TFA in H2O, B: 0. 05% TFA in CH3CN ; 10% B to 95% B over 15 minutes, hold for 5 minutes; X 240 nm, 1 ml/min

The synthetic route of 171178-47-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2005/16926; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 171178-47-5, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 171178-47-5 as follows.

COMPOUND EXAMPLE 16 Trans-4- [6- (4-HYDROXY-3-METHOXY-BENZYLCARBAMOYL)-4-OXO-4H-PYRIDO [3,4- d] pyrimidin-3-ylmethyl] -cyclohexanecarboxylic acid Step (a): 4-oxo-3, 4-dihydro-pyrido [3, 4-D] PYRIDINE-6-CARBOXYLIC acid methyl ester A solution of 6-chloro-3H-pyrido [3,4-d] pyrimidin-4-one (20.76g, 114. 3mmol), in 350mL of methanol was treated with triethylamine (39.8mL, 286MMOL), and dppf-PdC12 (1.87g, 2. 29MMOL), and the mixture was heated at 100C under 500psi of CO for 14 hours. The reaction mixture was cooled to room temperature. The resulting solid was collected by filtration, washed with methanol, washed with ethyl acetate, and dried to give 20.72g of 4-oxo-3,4- dihydro-pyrido [3, 4-D] PYRIDINE-6-CARBOXYLIC acid methyl ester as a gray solid (88. 3% yield). 1H NMR (400 MHz, DMSO-D6) delta (ppm) 3.9 (s, 3H), 8.3 (s, 1H), 8.5 (s, 1H), 9.1 (s, 1H), 12.8 (bs, 1H) MS (APCI) M + 1 = 206. 1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,171178-47-5, its application will become more common.

Reference:
Patent; WARNER-LAMBERT COMPANY LLC; WO2005/16926; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia