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