Category: 7627-39-6

Reference of 7627-39-6, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 7627-39-6, name is 2,4-Dichloro-5-(ethoxymethyl)pyrimidine. A new synthetic method of this compound is introduced below.

[0133] To a stirred solution of 3-hydroxy-10-(methyl-d3)-9,10,11,12-tetrahydro-8H- [1,4]diazepino[5′,6′:4,5]thieno[3,2-f]quinolin-8-one-10,11,11-d3 (INT-1) (200.0 mg, 0.6 mmol) in DMSO (4 mL) was added K2CO3 (180.8 mg, 1.3 mmol) and stirred at room temperature for 40 mins followed by addition of 2,4-dichloro-5-(ethoxymethyl)pyrimidine (203.4 mg, 1.0 mmol). This reaction mixture was stirred at room temperature overnight. LCMS showed the reaction was complete. The reaction mixture was passed though silica gel and purified by reverse phase prep-HPLC to afford 3-((2-chloro-5-(ethoxymethyl)pyrimidin-4-yl)oxy)-10-(methyl-d3)- 9,10,11,12-tetrahydro-8H-[1,4]diazepino[5′,6′:4,5]thieno[3,2-f]quinolin-8-one-10,11,11-d3 (I-2) (111.1 mg, 39.0%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) delta 9.36 (d, J = 9.0 Hz, 1H), 8.71 (s, 1H), 8.19 (s, J = 9.0 Hz, 1H), 8.12 (s, 1H), 7.86 (d, J = 9.0 Hz, 1H), 7.63 (d, J = 9.0 Hz, 1H), 4.66 (s, 1H), 3.62 (dd, J = 4.0 Hz, 2H), 1.20 (t, J = 4.0 Hz, 3H). MS m/z (M+H): 476.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7627-39-6, its application will become more common.

Reference:
Patent; CELGENE CAR LLC; MALONA, John; SURAPANENI, Sekhar S.; (116 pag.)WO2018/170201; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 7627-39-6, name is 2,4-Dichloro-5-(ethoxymethyl)pyrimidine, the common compound, a new synthetic route is introduced below. Product Details of 7627-39-6

Sodium bicarbonate (700.67 mg, 8.34 mmol) was added to 4 mL of dry DMSO.2,4-dichloro-5 -(ethoxymethyl)pyrimidine (172.7 mg, 0.8300 mmol) was added followed by glutathione (256.32 mg, 0.83 00 mmol). The reaction was stirred at room temperature for 48 h. Once judged complete, the reaction was filtered and then diluted with 0.5 mL of water and purified directly by reverse phase prep-HPLC (10-95% MeCN/Water, 0.1% TFA) to give (2S)-2- amino-5 -oxo-5 – [[( 1R)-2-(carboxymethylamino)- 1 -[ [2-chloro-5 -(ethoxymethyl)pyrimidin-4- yl]sulfanylmethyl]-2-oxo-ethyl]amino]pentanoic acid (25 mg, 0.0523 mmol, 6.3 % yield) (VI-) MS m/z (M+H)= 478.14.

The synthetic route of 7627-39-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELGENE CAR LLC; GUO, Jian; MALONA, John; RUCHELMAN, Alexander L.; SURAPANENI, Sekhar S.; (158 pag.)WO2018/170200; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 7627-39-6, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 7627-39-6, name is 2,4-Dichloro-5-(ethoxymethyl)pyrimidine. A new synthetic method of this compound is introduced below.

A yellow slurry mixture of (S)-3-hydroxy-10-methyl-9,10,1 1,12-tetrahydro-8H- [1 ,4]diazepino[5?,6? :4, 5]thieno[3 ,2-f]quinolin-8-one (30 g, 100 mmol), 2,4-dichloro-5- (ethoxymethyl)pyrimidine (24.90 g, 120 mmol), and potassium carbonate (325 mesh) (16.96 g, 120 mmol) in DMSO (150 ml, 2114 mmol) and THF (150 ml, 1831 mmol) was stirred at ambient temperature for 5 – 10 minutes, followed by heating at 40 – 45 C for at least 16 hours with sufficient agitation (350 – 400 rpm). The yellow/tan slurry mixture was then cooled to 20 – 25 C, and filtered over 9 g of Celite (prewetted with 15 mL of THF). The yellow filtrate (400 ml) was transferred back to the visually clean jacketed flask along with 240 mL of THF, and was heated to 40-45 C over 30 minutes. To the mixture was charged 150 mL of 10 wt% aqueous NaC1, stirred for 5 minutes and settled for phase split. After the bottom aqueous phase was removed, 150 mL of THF and 150 mL of 10 wt% aqueous NaC1 were charged and stirred at 40- 45 C for 5 minutes. The aqueous phase was removed again. Then, 90 mL of THF and 50 mL of 10 wt% aqueous NaC1 were charged, maintaining the batch temp at 40-45 C (lower temp will make product crystallize out). The aqueous phase was removed and the remaining organic portion was distilled under atmospheric pressure at 65-70 C to 300 ml. The batch was seeded with 200 mg of the product and the resulting mixture was aged for one hour. Then the batch was distilled with addition of isopropanol (600 ml) at a rate sufficient to maintain a constant batch volume. The slurry was cooled from 70 C to 22 C over 4 hours, hold at 22 C for 16 hours and filtered, washed with 3 x 30 mL of IPA, and dried in a vacuum oven at 40-45 C for 12-16 hours to afford compound? as a yellow solid (41.1 g, 87% yield); HPLC: Waters Ascentis Express C-18 HPLC column, 10 cm X 4.6 tm, 1 mL/min, 234 nm, gradient at 100% 0.1% H3P04 to 100% CH3CN in 10 mm, then hold at 100% CH3CN for 5 mm): tR= 6.40 mm (99.0%). ?H NMR (300 IVIHz, DMSO-d6) ppm 1.13 – 1.27 (m, 6 H) 3.42-3.54 (m, 2 H) 3.57-3.70 (m, 3 H) 4.66 (s, 2 H) 7.18 (brt, J=5.18 Hz, 1 H) 7.64 (d, J=9.08 Hz, 1 H) 7.87 (d, J=8.89 Hz, 1 H)8.12 – 8.23 (m, 2 H) 8.72 (s, 1 H) 9.37 (d, J=9. 17 Hz, 1 H); ?3C NMR (75 IVIFIz, DMSO-d6) ppm 15.47, 19.12, 48.46, 52.39, 64.02, 66.28, 114.87, 115.10, 119.60, 124.30, 126.49, 126.75, 127.7, 135.77, 139.30, 145.00, 145.84, 156.32, 158.02, 160.48, 164.52, 167.37. LC/IVIS m/e=470. Anal. Calcd. for C22H20N503SC1: C, 56.23; H, 4.29; N, 14.90; S, 6.82; Cl, 7.54. Found: C, 55.87; H, 4.33; N, 14.61; S, 6.60.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7627-39-6, 2,4-Dichloro-5-(ethoxymethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; CELGENE CAR LLC; FEIGELSON, Gregg Brian; GEHERTY, Maryll, E.; HEID, JR., Richard Martin; KOTHARE, Mohit; MAN, Hon-Wah; RUCHELMAN, Alexander L.; TRAVERSE, John F.; YONG, Kelvin Hin-Yeong; ZHANG, Chengmin; (123 pag.)WO2018/170203; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 7627-39-6, 2,4-Dichloro-5-(ethoxymethyl)pyrimidine, 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, Recommanded Product: 2,4-Dichloro-5-(ethoxymethyl)pyrimidine, blongs to pyrimidines compound. Recommanded Product: 2,4-Dichloro-5-(ethoxymethyl)pyrimidine

A yellow slurry mixture of (S)-3 -hydroxy- 10-methyl-9, 10, 11,12-tetrahydro-8H- [l,4]diazepino[5′,6′:4,5]thieno[3,2-f]quinolin-8-one (30 g, 100 mmol), 2,4-dichloro-5- (ethoxymethyl)pyrimidine (24.90 g, 120 mmol), and potassium carbonate (325 mesh) (16.96 g, 120 mmol) in DMSO (150 ml, 2114 mmol) and THF (150 ml, 1831 mmol) was stirred at ambient temperature for 5 – 10 minutes, followed by heating at 40 – 45 C for at least 16 hours with sufficient agitation (350 – 400 rpm). The yellow/tan slurry mixture was then cooled to 20 – 25 C, and filtered over 9 g of Celite (prewetted with 15 mL of THF). The yellow filtrate (-400 ml) was transferred back to the visually clean jacketed flask along with 240 mL of THF, and was heated to 40-45 C over 30 minutes. To the mixture was charged 150 mL of 10 wt% aqueous NaCl, stirred for 5 minutes and settled for phase split. After the bottom aqueous phase was removed, 150 mL of THF and 150 mL of 10 wt% aqueous NaCl were charged and stirred at 40- 45 C for 5 minutes. The aqueous phase was removed again. Then, 90 mL of THF and 50 mL of 10 wt% aqueous NaCl were charged,maintining the batch temp at 40-45 C (lower temp will make product crystallize out). The aqueous phase was removed and the remaining organic portion was distilled under atmospheric pressure at 65-70 C to ~ 300 ml. The batch was seeded with 200 mg of the product and the resulting mixture was aged for one hour. Then the batch was distilled with addition of isopropanol (600 ml) at a rate sufficient to maintain a constant batch volume. The slurry was cooled from -70 C to 22 C over 4 hours, hold at 22 C for 16 hours and filtered, washed with 3 x 30 mL of IP A, and dried in a vacuum oven at 40-45 C for 12-16 hours to afford a yellow solid (41.1 g, 87% yield); HPLC: Waters Ascentis Express C-18 HPLC column, 10 cm X 4.6 muiotaeta, 1 mL/min, 234 nm, gradient at 100% 0.1% H3P04to 100% CH3CN in 10 min, then hold at 100% CH3CN for 5 min): tR= 6.40 min (99.0%). 1H NMR (300 MHz, DMSO-i) delta ppm 1.13 – 1.27 (m, 6 H) 3.42 – 3.54 (m, 2 H) 3.57 – 3.70 (m, 3 H) 4.66 (s, 2 H) 7.18 (br t, J=5.18 Hz, 1 H) 7.64 (d, J=9.08 Hz, 1 H) 7.87 (d, J=8.89 Hz, 1 H) 8.12 – 8.23 (m, 2 H) 8.72 (s, 1 H) 9.37 (d, J=9.17 Hz, 1 H);13C NMR (75 MHz, DMSO- ) delta ppm 15.47, 19.12, 48.46, 52.39, 64.02, 66.28, 114.87, 115.10, 119.60, 124.30, 126.49, 126.75, 127.7, 135.77, 139.30, 145.00, 145.84, 156.32, 158.02, 160.48, 164.52, 167.37. LC/MS m/e+= 470. Anal. Calcd. for C22H2oN503SCl: C, 56.23; H, 4.29; N, 14.90; S, 6.82; CI, 7.54. Found: C, 55.87; H, 4.33; N, 14.61; S, 6.60.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7627-39-6, 2,4-Dichloro-5-(ethoxymethyl)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; CELGENE CAR LLC; MALONA, John; RUCHELMAN, Alexander L.; (117 pag.)WO2018/170204; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia