Pyrimidines

Electric Literature of 63931-21-5 ,Some common heterocyclic compound, 63931-21-5, molecular formula is C4BrCl3N2, 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.

5-Bromo-2,4,6-trichloropyrimidine (1.880 g, 6.81 mmol) was dissolved in THF (11 mL) and water (5 mL), and sodium acetate (1.68 g, 20.4 mmol), followed by 4-fluoroaniline (787 mg, 0.68 mL, 6.87 mmol) were added. The mixture was stirred at room temperature for 18 h. After that, a saturated aqueous solution of sodium hydrogencarbonate (15 mL) was added and the resulting mixture was extracted with ethyl acetate (2 x 150 mL). The combined organic layers were dried (sodium sulfate) and concentrated in vacuo. The crude was purified by column chromatography (silica gel, 40 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 10:90) to afford, after drying in vacuo (40C, 5 mbar), the title compound as a light brown solid (2.07 g, 90%). HPLC (method LCMS_fastgradient) tR = 1.36 min. 1H NMR (CDC13, 300 MHz): delta 7.12 (dd, / = 8.3, 9.1 Hz, 2 H), 7.43 (br s, 1 H), 7.52 (dd, / = 4.6, 8.9 Hz, 2 H). MS (ES+) m/z 335.9, 337.9, 339.9 [M+H, Br & 2 CI isotopes] .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,63931-21-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; JAKOB-ROETNE, Roland; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; STEINER, Sandra; (89 pag.)WO2018/11164; (2018); A1;,
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Synthetic Route of 16019-33-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 16019-33-3 as follows.

Step 1 : 7-(4-Bromo-3-fluorophenyl)-4-chloro-6,7-dihydro-5H-pyrrolo[2,3- c/]pyrimidine (141) A round bottom flask was charged with 4-bromo-3-fluoroaniline (10.0 g, 52.5 mmol) and then cooled to -150C. Trifluoroacetic acid (50 ml.) was added to the above cold aniline while stirring the contents for 0.5 h. Na(OAc)3BH (15.9 g, 50 mmol) was added portion wise to the above mixture and stirred for additional 0.5 h. The aldehyde 209 (see example 118, step 1 , 7.85 g, 75 mmol) in CH2CI2 (15 ml.) was added to the above mixture. The resultant mixture was allowed to warm up to the ambient temperature and stirred for 24 h. The reaction mixture was concentrated under reduced pressure and the residue was poured into sat. NaHCO3 solution (250 ml.) and then the mixture was extracted with CH2CI2 (3 x 250 ml_). The combined organic layer was washed with brine (1 x 100 ml_), dried over sat. Na2SO4 and then concentrated under reduced pressure to afford crude material, which was recrystallized from CH2CI2 and MeOH to afford 8.65 g (53%) of the title prodcuct 141_as an off-white solid. 1H NMR (400 MHz, DMSO-c/6): delta 8.42 (s, 1 H), 7.88 and 7.86 (dd, J1 = 11.2 Hz, J2 = 2.8 Hz, 2 H), 7.51 (t, J = 8.0 Hz, 1 H), 7.36 and 7.34 (dd, J1 = 9.2 Hz, J2 = 2.4 Hz, 1 H), 4.11 (t, J = 8.8 Hz, 2 H), 3.22 (t, J = 8.4 Hz, 2 H); LCMS (ESI): m/z 329 (M + H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16019-33-3, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/8895; (2008); A1;,
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Related Products of 6299-25-8 ,Some common heterocyclic compound, 6299-25-8, molecular formula is C5H4Cl2N2S, 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.

4,6-dichloro-2-(methylthio)pyrimidine (0.7?g, 3.608?mmol) was dissolved in dichloromethane (15?mL), cooled to 0?C and meta-Chloroperoxybenzoic acid (m-CPBA) was added (1.55?g, 9.011?mmol) portion wise to the reaction mixture at the same temperature. After addition, the reaction mixture was allowed to stir for 4?h at room temperature. Then the reaction mass was quenched with an aqueous solution of sodium thiosulphate (11?mL) and extracted with dichloromethane (2?*?10?mL). Combined organic layer was washed with saturated aqueous NaHCO3 solution (15?mL), brine solution (7?mL), dried over anhydrous MgSO4, filtered and the filtrate was evaporated under reduced pressure to afford 4,6-dichloro-2-(methylsulfonyl)pyrimidine (0.65?g, 80.20%) as off-white solid ( Scheme -1).

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. 6299-25-8, 4,6-Dichloro-2-(methylthio)pyrimidine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Murthy, P. Krishna; Valverde, Clodoaldo; Suneetha; Armakovi?, Stevan; Armakovi?, Sanja J.; Rani, N. Usha; Naidu, N. Venkatasubba; Journal of Molecular Structure; vol. 1186; (2019); p. 263 – 275;,
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Synthetic Route of 98136-42-6, 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 98136-42-6, name is 2,6-Dichloropyrimidine-4-carboxamide. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2,6-dichloropyrimidine-4-carboxamide (0.385 g, 2.01 mmol) in THF (10 mL) was added (S)-ethyl 2-hydroxypropanoate (0.26 mL, 2.3 mmol). The mixture was cooled on a dry-ice acetone bath and 60% NaH in mineral oil (0.094 g, 2.4 mmol) was added. The reaction was allowed to warm up slowly and after 2 h was quenched with 2 mL 10% citric acid solution. The reaction mixture was partitioned between 50 mL EtOAc and 25 mL brine and the organic fraction dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved in dioxane (10 mL) and 2-(4-(4-fluorophenoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.691 g, 2.20 mmol), 2M aqueous Na2CO3 (2.0 mL, 4.0 mmol), and PdCl2(dppf) (0.091 g, 0.1 1 mmol) were added. The reaction vessel was flushed with argon, sealed, and heated at 100C overnight. After cooling, the reaction mixture was evaporated in vacuo and the residue chromatographed over silica gel with 10-50% acetone in hexanes. The product fractions were evaporated in vacuo to give (S)-ethyl 2-((6-carbamoyl-2-(4-(4-fluorophenoxy)phenyl)pyrimidin-4-yl)oxy)propanoate as a pale tan oil (0.762 g, 1.79 mmol, 90% yield).

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 98136-42-6, 2,6-Dichloropyrimidine-4-carboxamide.

Reference:
Patent; PURDUE PHARMA L.P.; LOCKMAN, Jeffrey; NI, Chiyou; PARK, Jae Hyun; PARK, Minnie; SHAO, Bin; TAFESSE, Laykea; YAO, Jiangchao; YOUNGMAN, Mark, A.; WO2014/135955; (2014); A1;,
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Synthetic Route of 289042-12-2, 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. 289042-12-2, name is tert-Butyl 2-((4R,6S)-6-((E)-2-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl)vinyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate. A new synthetic method of this compound is introduced below.

The method for synthesizing the rosuvastatin calcium chiral isomer impurity of the present embodiment comprises the following steps:(1) 20g compound I was added to 500mL three reaction flask, stirred and dissolved in 220mL of acetonitrile was added dropwise 60mL 0.05M hydrochloric acid, the reaction was incubated dropwise at 35 ~ 40 C for 3 hours until the starting material disappeared (TLC: Ester: petroleum ether = 6: 1),The pH was adjusted to neutral with 5% sodium bicarbonate solution, the acetonitrile was removed by distillation under reduced pressure, extracted twice with methylene chloride (100 mL * 2), dried over anhydrous sodium sulfate, filtered,The filtrate was transferred to 500mL three reaction flask, 60g of manganese dioxide was added, the reaction was refluxed for 20 hours, the reaction was over, filtered, the filtrate was evaporated under reduced pressure and concentrated to dryness to give 17.6g light yellow oil, namely compound III, directly into the next reaction; The yield of compound III was 95.2%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,289042-12-2, its application will become more common.

Reference:
Patent; Zhejiang Mei Nuohua Pharmaceutical Chemical Co., Ltd.; Yu Kui; Huang Xiangliang; Jia Jiangnan; Liu Tao; Yu Shenggang; Lin Zufeng; Chen Weiren; Yao Chengzhi; (12 pag.)CN107382875; (2017); A;,
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Electric Literature of 50593-92-5, Adding some certain compound to certain chemical reactions, such as: 50593-92-5, name is 5-Bromo-2-(methylthio)pyrimidine-4-carboxylic acid,molecular formula is C6H5BrN2O2S, 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 50593-92-5.

(b). 2-Methylsulfanyl-pyrimidine-4-carboxylic acid; The product of example 21a (517 mg) in methanol (25 ml) was hydrogenated in a PARR apparatus in the presence of KOH (260 mg) and 10% Pd on BaSO4 (260 mg) for4 h. The reaction mixture was filtered over decalite and washed with methanol (warm), The filtrate was concentrated to 50% of its volume followed by addition of cone. HCl(33%) to pH 1. The precipitate (KBr) was filtered off and the mother liquor was concentrated in vacuo. The residue was recrystallized from dioxane. Yield: 200 mg. MS-ESI: [M+H]+ = 170

According to the analysis of related databases, 50593-92-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N.V. ORGANON; WO2006/117368; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 591-55-9, 5-Aminopyrimidine, 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, 591-55-9, blongs to pyrimidines compound. Formula: C4H5N3

aminopyrimidine (2) (504mg, 5.0mmol), 2-chloropyrazine (1) (0.54mL, 6.0mmol), Pd2(dba)3 (138mg, 0.15mmol), XantPhos (175mg, 0.30mmol) and Cs2C03 (3.29g, 10.1 mmol) were added sequentially with continued degassing. The reaction mixture was degassed with Ar(g) for a further 10min then heated up to 90C overnight. Once cooled down to rt, it was poured into H20 (25ml_) and extracted with EtOAc (3 x 35ml_). The combined organic extracts were dried over MgS04, filtered, concentrated in vacuo and purified by silica gel column chromatography with CH2CI2/MeOH (1 :0-12: 1 ). The residue was re-dissolved in CH2CI2/MeOH (4: 1 , 50ml_) and swirled with MP-TMT resin (1.2g, 1.3mmol/g) at rt overnight. The solution was filtered, the resin washed with CH2CI2/MeOH (4:1 , 100ml_) and the filtrate concentrated in vacuo. Purification by silica gel column chromatography with EtOAc/MeOH (1 :0-16:1 ) then reverse-phase column chromatography with H20/MeCN (1 :0-9: 1 ) yielded (3) as an off-white solid (66mg, 8%). (0709) LCMS (ES): Found 174.1 [M+Hf.1H NMR (300 MHz, DMSO-cf6), d: 9.13 (s, 2H), 8.77 (s, 1 H), 8.30 (d, J=1.3 Hz, 1 H), 8.20 (dd, J= 2.8, 1.3 Hz, 1 H), 8.04 (d, J= 2.8 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,591-55-9, its application will become more common.

Reference:
Patent; KARUS THERAPEUTICS LIMITED; SHUTTLEWORTH, Stephen Joseph; GATLAND, Alice Elizabeth; FINNEMORE, Daniel John; ALEXANDER, Rikki Peter; SILVA, Franck; CECIL, Alexander; (233 pag.)WO2019/166824; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 17573-78-3, 4,5,6-Trifluoropyrimidine, 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, 17573-78-3, blongs to pyrimidines compound. Formula: C4HF3N2

Example 1 To a mixture obtained by adding 110.0 g of 4,5,6-trifluoropyrimidine, 114.6 g of potassium carbonate and 16.6 g of triethylamine to 220.0 g of toluene, 60.4 g of 2-butyn-1-ol is added dropwise at 25 to 30C over one hour, followed by stirring at 30C. Then, 220.0 g of water is added dropwise into the reaction mixture, followed by stirring. Then, 85.4 g of 3, 3-dimethylpyrrolidine is added dropwise and, after the mixture is stirred at 30C, the reaction mixture is allowed to stand. After separating into the organic layer and the aqueous layer, the aqueous layer is removed and the organic layer is washed once with 220.0 g of 5% hydrochloric acid and then washed once with 220.0 g of water. The organic layer is concentrated to obtain 4-(2-butynyloxy)-5-fluoro-6-(3,3-dimethylpyrrolidin-1-yl)py rimidine (hereinafter referred to as the present compound (1)).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17573-78-3, its application will become more common.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2011795; (2009); A1;,
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Synthetic Route of 3438-46-8 ,Some common heterocyclic compound, 3438-46-8, molecular formula is C5H6N2, 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.

PREPARATION H 4-Formylpyrimidine A solution of 4-methylpyrimidine (10 g, 0.106 mole) in 100 ml dioxane was treated with 11.8 g selenium dioxide at room temperature and the mixture was heated at 100 C. for 15 hours. After adding 2.5 g selenium dioxide, heating was continued one hour, the mixture cooled, filtered, and the cake washed with ethyl acetate. The filtrate and washings were evaporated to dryness in vacuo . The residual dark oil was taken up in methylene chloride, filtered and the solvent evaporated. The residue was crystallized from a small amount of methylene chloride to provide the title aldehyde. 1H-NMR(CDCl3)ppm (delta): 7.87 (dd, 1H), 9.06 (d, 1H), 9.43 (d, 1H), 10.0 (s, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3438-46-8, its application will become more common.

Reference:
Patent; PFIZER INC.; EP150984; (1991); B1;,
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Related Products of 23945-44-0, 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.23945-44-0, name is 2,4-Dihydroxypyrimidine-5-carboxylic acid, molecular formula is C5H4N2O4, molecular weight is 156.0963, as common compound, the synthetic route is as follows.

To a 25 ml three-necked flask was added uracil-5-carboxylic acid (1 g, 6.4 mmol)N, N-dimethylaniline (1.09 g, 9. 0 mmol) was added dropwise to a solution of phosphorus oxychloride (9.83 g, 64. lmmol) under ice-cooling.After the dropwise addition, the ice bath was heated to 110 C for 4 hours. After the reaction solution was cooled, it was slowly added to the ice water for quenching.The aqueous phase was extracted with ethyl acetate and the organic phase was washed twice with water, once with saturated brine, dried over anhydrous sodium sulfate and concentrated to give 960 mg of crude oil as an oil, 2,4-dichloro-5-pyrimidinecarboxylic acid Purification is used directly for the next step

Statistics shows that 23945-44-0 is playing an increasingly important role. we look forward to future research findings about 2,4-Dihydroxypyrimidine-5-carboxylic acid.

Reference:
Patent; SUZHOU WANGSHAN WANGSHUI BIOMEDICAL CO LTD; TOPHARMAN SHANGHAI CO LTD; SHANDONG TOPHARMAN PHARMACEUTICAL CO LTD; TIAN, GUANGHUI; LI, JUNQI; (17 pag.)CN104650045; (2017); B;,
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