Category: pyrimidines

Reference of 1780-38-7, 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.1780-38-7, name is 2,4,6-Trichloro-5-ethylpyrimidine, molecular formula is C6H5Cl3N2, molecular weight is 211.48, as common compound, the synthetic route is as follows.

Example I 2,4-Bis-benzyloxy-6-chloro-5-ethyl-pyrimidine (39): To a stirred solution of benzyl alcohol (80 ml) in water bath, was added sodium metal (2.17 g, 94.6 mmol) under nitrogen atmosphere. After complete reaction of sodium metal, the mixture was cooled in an ice bath and 2,4,6-Trichloro-5-ethyl-pyrimidine (10.5 g, 49.6 mmol) was added portionwise. After stirring for 30 min in an ice bath, the reaction mixture was stirred at room temperature for overnight. Excess benzyl alcohol was evaporated in vacuo and the residue was dissolved in ether, washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a pale yellow oil. The crude product was purified by silica gel column chromatography (eluent, ether:hexane (4:96)) to give 14 g (80percent) of a white solid; m.p. 53-54° C.; 1H NMR (200 MHz, CDCl3) delta: 1.14 (3H, t, J=7.4 Hz), 2.70 (2H, q, J=7.4 Hz), 5.41 (2H, s), 5.45 (2H, s), 7.34-7.53 (10H, m); m/z (EI): 354(M+).

The chemical industry reduces the impact on the environment during synthesis 1780-38-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Guo, Hongyan; Kim, Choung U.; Kim, Hae Soo; Lee, Chong-Kyo; Lee, Ill Young; Mitchell, Michael L.; Son, Jong Chan; Xu, Lianhong; US2008/70920; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 31169-25-2, 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. 31169-25-2, name is 7-Bromothieno[3,2-d]pyrimidin-4(3H)-one, molecular formula is C6H3BrN2OS, 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.

7-Bromothieno[3,2-d]pyrimidine-4(3H)-one (5.9g) was dissolved in POCl3 (20mL) and then stirred at 150°C for 3 hours. After cooling down to room temperature, the remaining POCI3 was concentrated and added to ice water to obtain a solid. The solid was washed with sat. NaHC03 solution and dried with N2 gas to obtain the title compound. NMR (400MHz, DMSO-d^) delta 9.16 (s, 1H), 8.79 (s, 1H).

According to the analysis of related databases, 31169-25-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HANMI HOLDINGS CO., LTD.; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; CATHOLIC UNIVERSITY INDUSTRY ACADEMIC COOPERATION FOUNDATION; SON, Jung Beom; JUNG, Seung Hyun; CHOI, Wha Il; JUNG, Young Hee; CHOI, Jae Yul; SONG, Ji Yeon; LEE, Kyu Hang; LEE, Jae Chul; KIM, Eun Young; AHN, Young Gil; KIM, Maeng Sup; CHOI, Hwan Geun; SIM, Tae Bo; HAM, Young Jin; PARK, Dong-sik; KIM, Hwan; KIM, Dong-Wook; WO2011/93684; (2011); A2;,
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Related Products of 5750-76-5 ,Some common heterocyclic compound, 5750-76-5, molecular formula is C4HCl3N2, 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.

To a solution of 2,4,5-trichloropyrimidine (7.0 g, 38.2 mmol) in MeOH (100 mL) was added sodium methoxide (4.1 g, 76.5 mmol) and the mixture was stirred at RT for l2h. The reaction mixture was evaporated to dryness and the residue purified by silica gel chromatography(Petroleum Ether/Ethyl Acetate = 20/1) to give 2,5-dichloro-4-methoxypyrimidine (5.1 g, 75%). MS Calcd.: 178, MS Found: 179 ([M+H]+).

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. 5750-76-5, 2,4,5-Trichloropyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; KINNATE BIOPHARMA INC.; KANOUNI, Toufike; ARNOLD, Lee D.; KALDOR, Stephen W.; MURPHY, Eric A.; TYHONAS, John; (0 pag.)WO2020/6497; (2020); A1;,
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Related Products of 14048-15-8, 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.14048-15-8, name is 2,4-Dimethoxypyrimidin-5-amine, molecular formula is C6H9N3O2, molecular weight is 155.16, as common compound, the synthetic route is as follows.

General Procedure for Synthesis; General procedure for 4-Aza-2,3-didehydropodophyllotoxin Sythesis (1). A mixture of substituted heteroaromatic amines (1 eq ), tetronic acid (1 eq), and a corresponding substituted aromatic aldehydes (1 eq) in EtOH (4 mL) was refluxed at temperature 78 oC for 1 h. The reaction mixture was allowed to cool to room temperature 25 oC. and the precipitated product was collected by vacuum filtration and washed with EtOH (3 mL) at room temperature 25 oC and then recrystallized with ethanol (15 mL and 78 oC) to give pure compounds in 90 – 98 % yield in all case.Example 12,4-dimethoxy-5-(3,4,5-trimethoxyphenyl)-5,6,8,9tetrahydrofuro[3′,4′:5,6]pyrido[2,3-iflpyrimidin-6-one (4a). This compound was prepared by method described above employing 3,4,5-trimethoxybenzaldehyde (200 mg, 1.020 mmol), tetronic acid (102 mg, 1.020 mmol) and 2,4-dimethoxypyrimidine-5-amine (158 mg, 1.020 mmol) to affords 4a, 390 mg in 92% yield. Mp: 299-300 C, NMR (200 MHz, DMSO-d6): (53.61 (s, 3H), 3.70 (s, 6H), 3.81 (s, 3H), 3.85 (s, 3H), 4.79-5.02 (m, 3H), 6.43 (s, 2H), 10.61 (s,lH); 13C NMR (75 MHz, DMSO-d6): £34.3, 53.8, 54.3, 55.7, 59.7, 65.2, 93.8, 99.6, 104.7, 136.1, 139.9, 152.4, 156.8, 163.2, 168.8, 171.1; MS (ESI): 416 [M++H]; HRMS (ESI) calcd for C20H22N3O7 ([M+Na]+) 416.1457; found: 416.1447.

Statistics shows that 14048-15-8 is playing an increasingly important role. we look forward to future research findings about 2,4-Dimethoxypyrimidin-5-amine.

Reference:
Patent; COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH; AHMED, Kamal; PAIDAKULA, Suresh; BANALA, Ashwini, Kumar; ADLA, Mallareddy; PAPAGARI, Venkat, Reddy; JAKI, Rasheed, Tamboli; WO2012/76942; (2012); A1;,
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Synthetic Route of 13223-25-1 , The common heterocyclic compound, 13223-25-1, name is 2-Chloro-4,6-dimethoxypyrimidine, molecular formula is C6H7ClN2O2, 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.

(a1) Preparation of 4,6-dimethoxy-2-(4-toluenesulfonyl)pyrimidine 4.38 g (25.0 mmol) of 2-chloro-4,6-dimethoxy-pyrimidine and 4.68 g (26.3 mmol) of sodium p-toluenesulfinate were heated in 25 ml of N,N-dimethylformamide to 100 C. while stirring. After 5 hours, the solvent was removed in a rotary evaporator at 60 C./20 mbar. The residue was taken up in 90 ml of water and 90 ml of ethyl acetate. After the organic phase had been separated off, the aqueous phase was again extracted with 75 ml of ethyl acetate. The combined organic phases was washed with water, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on a silica gel column (eluent hexane/ethyl acetate 4:1). The title product was obtained from the product fraction in the form of a white powder in a yield of 3.79 g (15 percent of theory). The melting point of the title compound was 129.2 to 133.4 C.

The synthetic route of 13223-25-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lonza AG; US5840892; (1998); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 5604-46-6, name is 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde, molecular formula is C5H3Cl2N3O, 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. Recommanded Product: 5604-46-6

1 (324 mg, 1.7 mmol) was dissolved in a mixed solution of 7 mL of tetrahydrofuran and water (3:1), warmed to 50 C, and hydrazine hydrate (170 mg, 3.3 mmol) was dissolved in 1.7 mL of water, slowly dripping Adding to the reaction solution, stirring for 40 min, the reaction solution was poured into 8 mL of ice water and stirred for 15 min, allowed to stand for 20 min, then filtered, and the filter cake was washed with acetone to obtain 0.23 g of pale yellow solid, yield 78.4%

With the rapid development of chemical substances, we look forward to future research findings about 5604-46-6.

Reference:
Patent; China Pharmaceutical University; Lai Yisheng; Di Rongrong; Ma Jun; Wang Lei; Liu Yu; Gu Mengyue; Kang Nannan; Li Yuezhen; (15 pag.)CN108371662; (2018); A;,
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Synthetic Route of 111196-81-7, Adding some certain compound to certain chemical reactions, such as: 111196-81-7, name is 2-Chloro-5-ethylpyrimidine,molecular formula is C6H7ClN2, 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 111196-81-7.

Step B: Preparation of 4-((lr,4r)-4-((l-(5-Ethylpyrimidin-2-yl)piperidin-4- yl)methoxy)cyclohexyl)nicotinonitrile (Compound 58).; A mixture of 4-((lr,4r)-4-(piperidin-4-ylmethoxy)cyclohexyl)nicotinonitriledihydrochloride (26.5 mg, 71.17 muetaiotaomicron), 2-chloro-5-ethylpyrimidine (43 mu, 0.354 mmol), and potassium carbonate (50 mg, 0.362 mmol) in 1 ml iPrOH was heated under microwave irradiation at 100C for 3 h. Mixture was extracted with water and CH2C12. Organic phases were dried over MgS04, filtered, and concentrated. Residue was purified by biotage CC (Si02, hexane/AcOEt gradient). Fractions containing product were concentrated and residue was re- purified by HPLC (CH3CN/H20 gradient + 0.1% TFA). Fractions containing product were partly concentrated and residue was extracted with 1 M NaOH and CH2C12. Organic phases were dried over MgS04, filtered, and concentrated to give 4-((lr,4r)-4-((l-(5-ethylpyrimidin-2- yl)piperidin-4-yl)methoxy)cyclohexyl)nicotinonitrile (22.1 mg, 54.50 muetaiotaomicron, 76.6 %) as a white solid. Exact mass calculated for C24H3iN50: 405.25, found: LCMS m/z = 406.4 (M+H+); lU NMR (400 MHz, CDC13) delta ppm 1.19-1.29 (m, 5H), 1.41-1.62 (m, 4H), 1.83-1.89 (m, 3H), 1.98- 2.04 (m, 2H), 2.20-2.26 (m, 2H), 2.47 (q, = 7.6, 2H), 2.86-2.97 (m, 3H), 3.27-3.35 (m, 1H), 3.38 (d, = 6.3 Hz, 2H), 4.71-4.77 (m, 2H), 7.28 (d, = 5.3 Hz, 1H), 8.18 (s, 2H), 8.71 (d, = 5.3 Hz, 1H), 8.82 (s, 1H).

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. 111196-81-7, 2-Chloro-5-ethylpyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert M.; HAN, Sangdon; LEHMANN, Juerg; THORESEN, Lars; WO2012/135570; (2012); A1;,
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Related Products of 19646-07-2 ,Some common heterocyclic compound, 19646-07-2, molecular formula is C5H4Cl2N2O, 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-Chloro-4,5-dimethoxy-pyrimidine To a solution of 10 g (55.9 mmol) 2,4-dich.oro-5-methoxy-pyrimidine in 200 mL MeOH was added 7.7 g (55.9 mmo.) K2CO3. The reaction mixture was stirred at room temperature for 24 h, then the volatiles were removed in vacuo. The residue was diluted with EtOAc (200 mL) and water (100 mL). The organic layer was separated, dried (Na2S04), and evaporated affording 9,0 g (92%) 2-chioro-4,5- dimethoxy-pyrimidine as a fluffy white solid which was used in subsequent steps without further purification. LCMS [M+H]+ =175.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,19646-07-2, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WOLKENBERG, Scott; HARRISON, Scott, T.; BARROW, James, C.; ZHAO, Zhijian; MELAMED, Jeffrey; KETT, Nathan; ZARTMAN, Amy; WO2011/109267; (2011); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 111196-81-7, 2-Chloro-5-ethylpyrimidine, 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, 111196-81-7, blongs to pyrimidines compound. name: 2-Chloro-5-ethylpyrimidine

To a solution of5-[4-(methanesulfonyl)phenyl]-1-(piperidin-4-yl)-1H-pyrazolo[3,4-c]pyridine hydrochloride (0.153 mmol) in dimethylsulfoxide (DMSO) (1.5 ml) were added 2-chloro-5-ethylpyrimidine (44 mg, 0.309mmol) and Cs2CO3 (249 mg, 0.734 mmol). The mixture wasstirred at 180 C under microwaveirradiation for 20 min. The reaction was diluted with water andextracted with ethyl acetate. The combined organic layers were dried overanhydrous Mg2SO4 and reduced under pressure. The residuewas purified by silica gel column chromatography (0-50% EtOAc in hexanes) toafford 20 as a colorless solid (44mg, 62% yield).1H NMR (300 MHz, CDCl3): delta ppm1.22 (t, J = 7.5 Hz, 3 H), 2.14 -2.25 (m, 2 H), 2.26 – 2.45 (m, 2 H), 2.50 (q, J = 7.5 Hz, 2 H), 3.10 (s, 3 H), 3.13 – 3.25 (m, 2 H), 4.81 – 4.93(m, 1 H), 4.93 – 5.03 (m, 2 H), 8.02 – 8.08 (m, 2 H), 8.11 – 8.14 (m, 2 H),8.20 – 8.27 (m, 4 H), 9.14 (s, 1 H).MS ESI/APCI Dual m/z: 463 [M+1]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,111196-81-7, its application will become more common.

Reference:
Article; Matsuda, Daisuke; Kobashi, Yohei; Mikami, Ayako; Kawamura, Madoka; Shiozawa, Fumiyasu; Kawabe, Kenichi; Hamada, Makoto; Oda, Koji; Nishimoto, Shinichi; Kimura, Kayo; Miyoshi, Masako; Takayama, Noriko; Kakinuma, Hiroyuki; Ohtake, Norikazu; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3441 – 3446;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 29274-22-4 ,Some common heterocyclic compound, 29274-22-4, molecular formula is C6H5N3O, 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.

A mixture of pyrazolo[l ,5-a]pyrimidin-5-ol (17.0 g, 126 mmol) inPOCI3 (100 mL) was heated at reflux for 3 hours. After cooling, the reaction was concentrated under vacuum. To the residue was added dichloromethane. The organic phase was carefully washed with saturated aqueous NaHC03 solution, dried and concentrated. The crude product was purified by passing through a short silica gel pad eluting with 50%> EtOAc in hexane to give 5-chloropyrazolo[l ,5-a]pyrimidine (13.1 g, 68%>).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,29274-22-4, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; ANDREWS, Steven W.; CONDROSKI, Kevin Ronald; DE MEESE, Lisa A.; FELL, Jay Bradford; FISCHER, John P.; LE HUEROU, Yvan; JOSEY, John A.; KOCH, Kevin; MIKNIS, Gregory F.; RODRIGUEZ, Martha E.; TOPALOV, George T.; WALLACE, Eli M.; XU, Rui; WO2011/29027; (2011); A1;,
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