Pyrimidines

Application of 62802-42-0, 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. 62802-42-0, name is 2-Chloro-5-fluoropyrimidine, molecular formula is C4H2ClFN2, 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.

[0642] Synthesis of 5-fluoropyrimidine-2-carbonitrile: [0643] To a stirred solution of 2-chloro-5-fluoropyrimidine (280 mg, 2.11 mmol) in DMA (6 mL) under argon atmosphere were added zinc cyanide (161 mg, 1.37 mmol), Pd2(dba)3 (77 mg, 0.08 mmol), dppf (93 mg, 0.16 mmol) and zinc (32 mg, 0.50 mmol) at room temperature; heated to 100 C and stirred for 20 min under Micro Wave irradiation. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was diluted with water (30 mL) and extracted with EtOAc (2 x 45 mL). The combined organic extracts were washed with water (40 mL), dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 7% EtOAc/ Hexanes to afford 5-fluoropyrimidine-2-carbonitrile (60 mg, 23%) as an off- white solid. [0644] 1H-NMR (CDC13, 400 MHz): delta 8.73 (s, 2H); TLC: 10% EtOAc/ Hexanes (R 0.4).

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 62802-42-0, 2-Chloro-5-fluoropyrimidine.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew, J.; BURSAVICH, Matthew, Gregory; WO2013/142269; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 514854-12-7, name is 6-Ethylpyrimidine-2,4-diamine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H10N4

A suspension of 2,4-diamino-6-ethylpyrimidine (0.8750 g, 5.00 mmol) and iodine monochloride (0.40 mL, 7.50 mmol) in methanol (15 mL) was stirred at roomtemperature for 2 hours. Water (5 mL) was added and adjusted pH to 7 with 10% aq NaOH. The reaction was extracted 3 times with ethyl acetate (15 mL each), dried over anhydrous MgSO4 and evaporated. The product was obtained as a light brown solid (1.1355 g, 86% yield).

With the rapid development of chemical substances, we look forward to future research findings about 514854-12-7.

Reference:
Patent; NATIONAL SCIENCE AND TECHNOLOGY DEVELOPMENT AGENCY; KAMCHONWONGPAISON, Sumalee; CHAROENSETAKUL, Netnapa; PEEWASAN, Krisana; VANICHTANANKUL, Jarunee; RATTANAJAK, Roonglawan; TAWEECHAI, Supannee; ANUKUNWITHAYA, Tosapol; YOOMUANG, Aphisit; YUTHAVONG, Yongyuth; VILAIVAN, Tirayut; (44 pag.)WO2017/52479; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 89487-99-0, name is 4-Hydroxy-2-(methylthio)pyrimidine-5-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 4-Hydroxy-2-(methylthio)pyrimidine-5-carbonitrile

Step B: A mixture of 4-hydroxy-2-methylsulfanyl-pyrimidine-5-carbonitrile (2.76 g) and phosphorus oxychloride (15 mL) was heated at reflux, under argon atmosphere, for 3 h. The reaction mixture was cooled and then evaporated under reduced pressure. Hexane was added to the residue and the mixture was heated at reflux, the resulting mixture was decanted and the same procedure was repeated for 4 times. The combined supernatant layers were evaporated to afford 1.13 g of 4-chloro-2-methylsulfanyl-pyrimidine-5-carbonitrile as a white powder.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 89487-99-0, 4-Hydroxy-2-(methylthio)pyrimidine-5-carbonitrile.

Reference:
Patent; Roche Palo Alto LLC; US2009/270389; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 5305-40-8, 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.5305-40-8, name is 4,6-Dichloropyrimidine-5-carbaldehyde, molecular formula is C5H2Cl2N2O, molecular weight is 176.9882, as common compound, the synthetic route is as follows.

Synthesis of Compound 4.1. Hydrazine hydrate (11.5 mL, 23.7 mmol) was slowly added to a solution of 4,6-dichloro-pyrimidine-5-carbaldehyde (40.0 g, 22.6 mmol), and triethylamine (30 mL, 22 mmol) in 1,4-dioxane (600 mL), while cooling to maintain an internal temperature below 20 C. After the addition was complete, the reaction was warmed to RT. After 1 hr, the reaction was filtered. The solvent was removed in vacuo to afford compound 4.1 (29 g, 83%) as a light yellow solid. 1H NMR (400.13 MHz, DMSO-d6) delta14.52 (br. s, 1H), 8.83 (s, 1H), 8.45 (s, 1H). MS m/z 155 [M+1]+.

Statistics shows that 5305-40-8 is playing an increasingly important role. we look forward to future research findings about 4,6-Dichloropyrimidine-5-carbaldehyde.

Reference:
Patent; Sunesis Pharmaceuticals, Inc; US2009/5359; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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.56686-16-9, name is 5-Bromo-2,4-dimethoxypyrimidine, molecular formula is C6H7BrN2O2, molecular weight is 219.04, as common compound, the synthetic route is as follows.Computed Properties of C6H7BrN2O2

A) 5-Chloro-3-(2,4-dimethoxypyrimidin-5-yl)-3-hydroxy-1,3-dihydroindol-2-one A 1.6 M solution of n-butyllithium in hexane (10 ml, 16 mmol) was added dropwise to a solution of 5-bromo-2,4-dimethoxypyrimidine (3.29 g, 15 mmol) in THF (50 ml) at -78 C. After stirring at -78 C. for 0.5 h, a suspension of 5-chloroisatin (1.27 g, 7.0 mmol) in THF (50 ml) was added dropwise. The reaction mixture was allowed to warm to room temperature and then saturated ammonium chloride solution was added. The mixture was extracted three times with ethyl acetate, and the combined organic layers were washed with saturated brine. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by chromatography (silica gel, 50% ethyl acetate in dichloromethane) resulted in 0.97 g of the product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56686-16-9, 5-Bromo-2,4-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Abbott GmbH & Co. KG; US2005/70718; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 183438-24-6, 5-Bromo-2-iodopyrimidine, 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, HPLC of Formula: C4H2BrIN2, blongs to pyrimidines compound. HPLC of Formula: C4H2BrIN2

Example 54: 5-bromo-2-(trifluoromethyl)pyrimidine:; A mixture of 1.77 g (30.35 mmoles, 1.33 eq.) of KF and 5.79 g (30.35 mmoles, 1.33 eq.) of CuI were stirred and heated together using a heat gun under vacuum (1 mm) for 20 min. After cooling, 20 ml_ of DMF and 20 ml of NMP were added followed by 4.1 ml_ (27.38 mmoles, 1.20 eq.) of CF3-TMS and 6.5 g (22.82 mmoles, 1.0 eq.) of 5-bromo-2- iodopyrimidine. The mixture was stirred at RT for 16h. The crude mixture was poured onto 200 ml_ of NH4OH 6N and the aqueous phase was extracted six times with 50 mL of AcOEt. The combined organic layers were washed three times with 50 mL of a saturated solution of Na2CO3, once with 50 mL of brine, dried over Na2SO4, filtered and evaporated to dryness. The crude compound was purified by flash chromatography on silica gel to give 940 mg of a white solid.Yield : 18 % M.P. : 33-39C EPO LC-MS : T1. = 4.32 min. (100 %) (no ionization)) [Column : Nucleosil C-18HD, 4×70 mm, 3mum, gradient CH3CN/H2O/TFA 0.05% : 20-100% CH3CN (6 min.), 100% CH3CN (1.5 min.), flow : 1 mL/min].1H-NMR (CDCI3, 300 MHz) delta : 8.93 (s, 2H). 19F-NMR (CDCI3, 282 MHz) delta : -70.8.

The synthetic route of 183438-24-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/136442; (2006); 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. 33097-11-9, name is 4,6-Dichloro-2-(methylthio)pyrimidine-5-carbaldehyde, the common compound, a new synthetic route is introduced below. COA of Formula: C6H4Cl2N2OS

4,6-Dichloro-2-methylsulfanyl-pyrimidine-5-carbaldehyde (7.54 g, 0.0338 mol) was added to 80 mL of dioxane and stirred for 10 minutes at room temperature. Diisopropyl ethylamine (6.03 mL, 0.0340 mol) was added and the mixture was cooled in an ice bath with stirring for 10 minutes. Anhydrous hydrazine (1.08 mL, 0.0338 mmol) was added dropwise over three minutes, and stirring was continued for an additional five minutes. The ice bath was removed, and the reaction ixture was heated to reflux with stirring for two hours. The reaction mixture was then stirred at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, and the residue was added to 20 mL of 2 N HCl and 100 mL EtOAc. The resulting suspension was stirred and filtered, ad the solid was washed with water followed by EtOAc. The organic phase of the filtrate was collected, and the aqueous phase was extracted three times with 150 mL EtOAc. The combined organic phases were dried (MgSO4), filtered, and the filtrate was evaporated under reduced pressure. The resulting solid was washed with diethyl ether/hexanes (1:1) and the solid was dried to provide 3.13 g of crude 4-Chloro-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine. Mass Spec. M+H=201.

The synthetic route of 33097-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2005/203091; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 126352-69-0, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 126352-69-0, name is 4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

(2) To acetic anhydride (0.153 ml) was added formic acid (0.077 ml) at 15-20 C. The mixture was stirred at ambient temperature for 30 minutes. To this solution was added 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (100 mg) under ice-cooling and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was added to a mixture of dichloromethane and aqueous sodium bicarbonate solution. The separated organic layer was dried over magnesium sulfate and evaporated in vacuo to give 4-formyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (79.9 mg). IR (Nujol): 1670, 1535, 1500, 1450, 1430, 1400 cm-1. NMR (DMSO-d6, delta): 1.97-2.27 (2H, m), 3.62-3.91 (2H, m), 3.97-4.24 (2H, m), 6.22 and 6.48 (1H, each d, J=3 Hz), 7.29 (1H, d, J=3 Hz), 8.19 and 8.77 (1H, each s).

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 126352-69-0, 4,5,6,7-Tetrahydropyrazolo[1,5-a]pyrimidine.

Reference:
Patent; Fujisawa Pharmaceutical Company, Ltd.; US5173485; (1992); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 6299-85-0, 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.6299-85-0, name is Methyl 2,6-dichloropyrimidine-4-carboxylate, molecular formula is C6H4Cl2N2O2, molecular weight is 207.0142, as common compound, the synthetic route is as follows.

Methyl 2,6-dichloropyrimidine-4-carboxylate (150 mg, 725 pmol) and [4-(trifluoromethyl)phenyl]boronic acid (124 mg, 652 pmol) were dissolved in 3 ml. dioxane, aqueous sodium carbonate solution (1.1 ml_, 2.0 M, 2.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (83.7 mg, 72.5 pmol) were added. The mixture was stirred for 2h at 90C. The reaction mixture was filtered and the precipitate was washed with DCM to give the title compound as a salt ( 350 mg, 0.69 mmol, 60% purity). LC-MS (Method 1 ): Rt = 0.69 min; MS (ESIneg): m/z = 301 [M-H]

The chemical industry reduces the impact on the environment during synthesis 6299-85-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; DEUTSCHES KREBSFORSCHUNGSZENTRUM; LEFRANC, Julien; SCHMEES, Norbert; ROeHN, Ulrike; ZORN, Ludwig; GUeNTHER, Judith; GUTCHER, Ilona; ROeSE, Lars; BADER, Benjamin; STOeCKIGT, Detlef; PLATTEN, Michael; (122 pag.)WO2019/101641; (2019); A1;,
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