Category: 108381-28-8

Application of 108381-28-8 ,Some common heterocyclic compound, 108381-28-8, molecular formula is C11H9ClN2O, 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.

First Step 2.6 g of 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenol and 1.7 g of 4-benzyloxy-2-chloropyrimidine were dissolved in 20 ml of N,N-dimethylformamide, to this solution was added 1.07 g of potassium carbonate, and the mixture was stirred for 2 hours at 80 C. The reaction solution was cooled to room temperature, then, this reaction solution was poured into ice water, and extracted with ethyl acetate. The organic layer was washed with 10% aqueous sodium hydroxide solution, dried over anhydrous magnesium sulfate, and concentrated to obtain 1.6 g of 4-benzyloxy-2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}pyrimidine.

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. 108381-28-8, 4-(Benzyloxy)-2-chloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sumitomo Chemical Company, Limited; US6537948; (2003); B1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 108381-28-8, 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. 108381-28-8, name is 4-(Benzyloxy)-2-chloropyrimidine, molecular formula is C11H9ClN2O, 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.

Step 1-Synthesis of 4-(benzyloxy)-N-(4-(4′-morpholino-5′,6′-dihydrospiro[cyclopropane-1,7′-pyrano[2,3-d]pyrimidine]-2′-yl)phenyl)pyrimidin-2-amine (cq): 4-(4′-morpholino-5′,6′-dihydrospiro[cyclopropane-1,7′-pyrano[2,3-d]pyrimidine]-2′-yl)aniline (co) (79.5 mg, 0.235 mmol), 4-(benzyloxy)-2-chloropyrimidine (63.4 mg, 0.287 mmol), bis(dibenzylideneacetone)palladium(0) (8.2 mg, 0.014 mmol), sodium tert-butoxide (35.8 mg, 0.372 mmol), and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (9.8 mg, 0.025 mmol) were weighed into a microwave vial. The vial was evacuated and purged 3× with N2, then degassed toluene (2.1 mL, 2.0E1 mmol) was added and the vial sealed. The reaction was microwaved at 120 C. for 20 min. The reaction mixture was filtered through Celite, washing extensively with CH2Cl2. This was then concentrated onto silica gel and subjected to column chromatography using a 12 g column, with a gradient of 0% to 100% ethyl acetate in hexanes. The product containing fractions were combined and evaporated under reduced pressure to give 4-(benzyloxy)-N-(4-(4′-morpholino-5′,6′-dihydrospiro[cyclopropane-1,7′-pyrano[2,3-d]pyrimidine]-2′-yl)phenyl)pyrimidin-2-amine: 1H NMR (400 MHz, DMSO) delta 8.75 (s, 1H), 8.12 (d, J=8.7 Hz, 2H), 7.45 (d, J=8.8 Hz, 2H), 6.98 (d, J=6.5 Hz, 1H), 4.81-4.67 (m, 3H), 4.44 (t, J=5.7 Hz, 2H), 3.79-3.69 (m, 4H), 3.48-3.40 (m, 4H), 2.71 (t, J=5.9 Hz, 2H), 1.86 (t, J=5.9 Hz, 2H), 1.01 (t, J=6.0 Hz, 2H), 0.73 (t, J=6.3 Hz, 2H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 108381-28-8, 4-(Benzyloxy)-2-chloropyrimidine.

Reference:
Patent; Genentech, Inc.; US2010/331305; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 108381-28-8, Adding some certain compound to certain chemical reactions, such as: 108381-28-8, name is 4-(Benzyloxy)-2-chloropyrimidine,molecular formula is C11H9ClN2O, 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 108381-28-8.

Step 1-Synthesis of (S)-4-(benzyloxy)-N-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)phenyl)pyrimidin-2-amine (cb): (S)-4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)aniline (ca) (68.6 mg1.00 equiv, 210.17 mumoles) was weighed into a microwave vial with a stirbar. 4-(benzyloxy)-2-chloropyrimidine (57.4 mg, 1.24 equiv, 260.13 mumoles), sodium t-butoxide (31.4 mg, 326.73 mmoles), bis(dibenzylideneacetone)palladium (8.6 mg14.96 mumoles) and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (7.3 mg18.55 mumoles) were added, then the reaction vial was evacuated and purged with N2 3 times. Toluene (2 mL) was added, and the reaction was heated in a CEM microwave at 120 C. for 40 minutes with PowerMax off. The reaction was then filtered through Celite, washing with CH2Cl2. The crude material was concentrated under reduced pressure onto silica gel, and was then purified using flash chromatography on a 4 g column using a gradient of 0% to 100% EtOAc in heptane. The product containing fractions were concentrated to give (S)-4-(benzyloxy)-N-(4-(4-(3-methylmorpholino)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidin-2-yl)phenyl)pyrimidin-2-amine (cb) (77 mg0.72 equiv150.80 mumoles71.75% yield) as an oil. 1H NMR (400 MHz, CDCl3) delta 8.40-8.33 (m, 2H), 8.18 (d, J=5.7, 1H), 7.66 (d, J=8.8, 2H), 7.49-7.30 (m, 5H), 6.28 (d, J=5.7, 1H), 5.44 (s, 2H), 4.48-4.29 (m, 2H), 4.09-3.45 (m, 6H), 2.72-2.49 (m, 2H), 2.03-1.91 (m, 2H), 1.72-1.50 (m, 2H), 1.34 (d, J=6.7, 3H).

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. 108381-28-8, 4-(Benzyloxy)-2-chloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Genentech, Inc.; US2010/331305; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 108381-28-8, 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. 108381-28-8, name is 4-(Benzyloxy)-2-chloropyrimidine, molecular formula is C11H9ClN2O, 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.

Step 1 In a microwave vial, cis-7-methyl-8-((3,4,5-trifluorophcnyl)carbamoyl)-2,3,3a,4,10,10a-hexahydro-lH,7H-dipyrrolo[3,4-b:3′,4′-f][l,4,5]oxathiazocin-2-ium 5,5-dioxide iodide (E11) (30 mg, 0.054 mmol) and 4-(benzyloxy)-2-chloropyrimidine (24 mg, 0.109 mmol) were suspended in 1-Butanol (0.5 mL), dry DIPEA (0.030 mL, 0.172 mmol) was added and mixture was heated at l20C under MW heating for lh. UPLC-MS showed complete conversion. The mixture was evaporated under reduced pressure to afford a brown solid. The residue was purified by preparative HPLC (H20, CEbCN 0.1% TFA) to afford, after lyophilization, 2-(4-(benzyloxy)pyrimidin-2-yl)-7-methyl-N-(3,4,5-trifluorophenyl)-2,3,3a,4,l0,l0a-hexahydro-lH,7H-dipyrrolo[3,4-b:3′,4′-f][l,4,5]oxathiazocine-8-carboxamide 5,5-dioxide as a beige powder (30 mg, yield=9l%). 4-(benzyloxy)-2-chloropyrimidine was present as impurity. Product was used in next step without further purification.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 108381-28-8, 4-(Benzyloxy)-2-chloropyrimidine.

Reference:
Patent; OSPEDALE SAN RAFFAELE S.R.L.; IRBM S.P.A.; PROMIDIS S.R.L.; ISTITUTO NAZIONALE DI GENETICA MOLECOLARE – INGM; DE FRANCESCO, Raffaele; DONNICI, Lorena; GUIDOTTI, Luca; IANNACONE, Matteo; DI FABIO, Romano; SUMMA, Vincenzo; PRANDI, Adolfo; RANDAZZO, Pietro; GORNATI, Davide; GRILLO, Alessandro; FERRANTE, Luca; BENCHEVA, Leda Ivanova; DE MATTEO, Marilenia; FERRARA, Marco; (238 pag.)WO2020/30781; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia