Pyrimidines

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. 2164-65-0, name is 2-Aminopyrimidine-4-carboxylic acid, molecular formula is C5H5N3O2, 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. Product Details of 2164-65-0

To a solution of the HCl salt of 38b, 2-amino-pyrimidine-4-carboxylic acid (30 mg, 0.22 mmol) and EEDQ (54 mg, 0.22 mmol) in DMF was added TEA (56 muL, 0.41 mmol). The reaction mixture was heated to 60 C. More reagent was added and the reaction was stirred at 65 C. until all 38b was consumed. The reaction was concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with a Magic/DCM gradient (0% to 20% Magic) which resulted in a slightly impure I-8, which was sequentially washed with DCM and MeOH to afford 6.3 mg of the desired product: MS calcd for C24H17ClN6O2S [M+H]+ 489. Found, 489: 1H NMR (DMSO-d6, 300 MHz): delta 10.49 (broad s, 1H), 8.66 (s, 1H), 8.53 (d, 1H), 7.99-7.79 (m, 5H), 7.48 (m, 4H), 7.16 (d, 1H), 6.95 (bs, 2H), 5.49 (s, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 2164-65-0.

Reference:
Patent; Roche Palo Alto LLC; US2011/70190; (2011); A1;,
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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. 1074-41-5, name is 6-Amino-2-(methylthio)pyrimidin-4-ol. This compound has unique chemical properties. The synthetic route is as follows. Safety of 6-Amino-2-(methylthio)pyrimidin-4-ol

General procedure: A mixture of equimolar amounts of 6-amino-2-(methylthio)pyrimidin-4(3H)-one (1) (1 mmol), ethylcyanoacetateor meldrum?s acid (2 or 5) (1 mmol) and aldehyde(3 or 6) (1 mmol) was added to a vial containinga magnetic stirring bar and [DMBSI]HSO4 (0.18 mmol,0.06g) and heated at 80 C in an oil bath. Stirring at 80C was continued until disappearance of the startingmaterials. At this stage, due to the poor solubility in theionic liquid, the product appears as a precipitate. Thereaction mixture was cooled and washed with water toextract the ionic liquid. The solid obtained was recrystallizedfrom ethanol to furnish the desired pure product.The ionic liquid was recovered from the aqueous extractsby evaporation under reduced pressure, and reusedin the next run.

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, 1074-41-5, 6-Amino-2-(methylthio)pyrimidin-4-ol.

Reference:
Article; Nia, Roghayeh Hossein; Mamaghani, Manouchehr; Tabatabaeian, Khalil; Shirini, Farhad; Rassa, Mehdi; Acta Chimica Slovenica; vol. 60; 4; (2013); p. 889 – 895;,
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Application of 330786-24-8 ,Some common heterocyclic compound, 330786-24-8, molecular formula is C17H13N5O, 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.

Step 1. To a solution of 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (300 mg, 1.0 mmole), triphenylphosphine (1.04 g, 3.96 mmole) and tert-butyl (2-hydroxyethyl)carbamate (238 mg, 1.5 mmoles) in THF (25 mL) was added DIAD (0.4 mL, 2mmoles). The reaction was stirred for 5 hrs at room temperature and then water (30 mL) was added and extracted with ethyl acetate. The organic layers were combined, washed with aq. NaHCO3 and brine, then dried (Na2SO4), filtered and concentrated. The resulting tert-butyl (2-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)carbamate was used without further purification.

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. 330786-24-8, 3-(4-Phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; BABLER, Martin; GERRITSEN, Mary E.; WO2014/22569; (2014); A1;,
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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. 157335-97-2, name is 5-Bromo-4,6-dimethylpyrimidine. A new synthetic method of this compound is introduced below., Recommanded Product: 157335-97-2

[1,1 ?-Bis(diphenylphosphino)ferrocene]dichloropalladium(l 1)-dichloromethanecomplex (5 g, 6 mmol) was added to a degassed mixture of 2-(4-methoxy-2-methylphenyl)-4,4,5,5-tetramethyl-1 ,3,2-dioxaborolane (30 g, 120 mmol), 5-bromo-4,6-dimethylpyrimidine (22.5 g, 120 mmol), and potassium phosphate (76.3 g, 359 mmol) in 1,4-dioxane (300 mL) and water (150 mL). The reaction mixture was heated at reflux for4 hours, whereupon it was filtered and concentrated in vacuo. Purification via silica gel chromatography (Gradient: ethyl acetate in petroleum ether) provided the product as abrown solid. Yield: 25 g, 110 mmol, 92%. LCMS m/z229.3 [M+H]. 1H NMR (300 MHz, ODd3) oe 8.95 (5, 1H), 6.94 (d, J=8.2 Hz, 1H), 6.87-6.89 (m, 1H), 6.84 (dd, J=8.3, 2.5 Hz, 1H), 3.86 (5, 3H), 2.21 (5, 6H), 1.99 (5, 3H).

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, 157335-97-2, 5-Bromo-4,6-dimethylpyrimidine.

Reference:
Patent; PFIZER INC.; GRAY, David Lawrence Firman; ZHANG, Lei; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/162515; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2927-71-1, 2,4-Dichloro-5-fluoropyrimidine, 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, Quality Control of 2,4-Dichloro-5-fluoropyrimidine, blongs to pyrimidines compound. Quality Control of 2,4-Dichloro-5-fluoropyrimidine

(1) Take 100g of 2,4-dichloro-5-fluoropyrimidine and dissolve it in 1000 ml of anhydrous tetrahydrofuran, lower it to a low temperature of 0 C, and add ammonia water dropwise. The speed of ammonia water drop control should be kept at When the temperature exceeds 0 , keep the temperature at 0 for 2 to 3 hours.(2) Naturally rise to room temperature for 1-2 hours, evaporate the solvent, dissolve in ethyl acetate, wash with saturated aqueous sodium bicarbonate solution, wash with saturated brine, dry, filter, and concentrate to obtain 2-chloro-4-amino-5-fluoropyrimidine And 2-amino-4-chloro-5-fluoropyrimidine 88 g;(3) The mixture obtained in step (2) is subjected to column chromatography to obtain 23.44 g of 2-amino-4-chloro-5-fluoropyrimidine, the purity is greater than 98%, and the yield is 26%.

The synthetic route of 2927-71-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Puruida Pharmaceutical Technology Co., Ltd.; Wang Xiaobo; (4 pag.)CN110343074; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 6693-08-9, 2,4,6-Trichloro-5-fluoropyrimidine, 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, Product Details of 6693-08-9, blongs to pyrimidines compound. Product Details of 6693-08-9

2,4,6-trichloro-5-fluoropyrimidine (2.21 g, 8.78 mmol),(+/-)-trans-3-aminobicyclo[2.2.2]octane-2-carboxylic acid methyl ester (1.75 g, 8.78 mmol)And K2CO3 (2.43 g, 17.60 mmol) was suspended in DMF (5 mL).The resulting suspension was stirred at room temperature overnight. The reaction was quenched by the addition of H 2 O (100 mL).The resulting mixture was extracted with ethyl acetate (50 mL×3).The combined organic phases were washed with saturated brine (80 mL×3).Dry over anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure.The residue was purified by silica gel column chromatography (EtOAc (EtOAc)The title compound was obtained as a white solid(2.71 g, 89%).

The synthetic route of 6693-08-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Ren Qingyun; Tang Changhua; Yin Junjun; Yi Kai; Lei Yibo; Wang Yejun; Zhang Yingjun; (138 pag.)CN108276401; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 153435-63-3, 2-(Tributylstannyl)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, 153435-63-3, blongs to pyrimidines compound. Formula: C16H30N2Sn

General procedure: Intermediates (D19-22 and D25-31) (1 mmol) were dissolved in dry DMF (15 ml/mmol) under nitrogen atmosphere, then CsF (2 mmol), CuI (0.2 mmol), [Ph3P]4Pd (0.1 mmol) and pyrimidine-2-tributylstannane (1.5 mmol; prepared according to Eur. J. Org. Chem. 2003, 1711-1721) were added. The mixture was warmed at 130 C. for 10 minutes (microwave), then poured in aqueous saturated solution of NH4Cl and extracted with AcOEt (3×50 ml). The organic layers were combined, dried (Na2SO4) and concentrated under vacuum; the crude mixture was purified by silica gel column chromatography (Cyclohexane 100% to Cyclohexane/Acetone 8/2 or Cyclohexane 100% to cyclohexane/AcOEt 2/8) to give the title compounds.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,153435-63-3, its application will become more common.

Reference:
Patent; Stasi, Luigi Piero; Rovati, Lucio Claudio; US2015/65523; (2015); A1;,
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Reference of 6299-85-0, 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. 6299-85-0, name is Methyl 2,6-dichloropyrimidine-4-carboxylate, molecular formula is C6H4Cl2N2O2, 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.

Methyl 2,6-dichloropyrimidine-4-carboxylate (1.00 g, 4.83 mmol) and [4- (trifluoromethoxy)phenyl]boronic acid (895 mg, 4.35 mmol) were dissolved in 20 ml. dioxane, sodium carbonate (7.2 ml_, 2.0 M, 14 mmol) and tetrakis(triphenylphosphine)palladium(0) (558 mg, 483 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 (2.47 g, 4.65 mmol, 60% purity).LC-MS (Method 1 ): Rt = 0.71 min; MS (ESIpos): m/z = 319 [M+H]+H-NMR (400MHz, DMSO-d6): d [ppm]= 7.57 (dd, 2H), 8.35 – 8.44 (m, 2H), 8.54 (s, 1 H)2-Chloro-6-[4-(trifluoromethoxy)phenyl]pyrimidine-4-carboxylic acid (1 1.2 g, 66 % purity, 23.2 mmol) and (3-fluorophenyl)boronic acid (4.88 g, 34.8 mmol) were solubilised in 1 ,4-dioxane (170 ml) and aqueous sodium carbonate (35 ml, 2.0 M, 70 mmol) was added. The reaction mixture was sparged with argon and palladiumtetrakis (2.68 g, 2.32 mmol) was added. The mixture was stirred for 5h at 80C. The mixture was evaporated and the residue was stirred in HCI (1 M) overnight and the solid was filtered, washed with water and dried under reduced pressure at 60C. The solid was then stirred in DCM/EtOH overnight, filtered, washed with DCM and dried under reduced pressure to give 3.89 g (98 % purity, 43 % yield) of the title compound that was used without further purification.LC-MS (method 2): Rt = 1.42 min; MS (ESIneg): m/z = 377 [M-H]1H-NMR (400MHz, DMSO-d6): d [ppm]= 7.35 – 7.42 (m, 1 H), 7.55 (d, 2H), 7.61 (td, 1 H), 8.1 1 (s, 1 H), 8.23 – 8.29 (m, 1 H), 8.36 – 8.41 (m, 1 H), 8.43 – 8.49 (m, 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 6299-85-0, Methyl 2,6-dichloropyrimidine-4-carboxylate.

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; (111 pag.)WO2019/101647; (2019); A1;,
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Related Products of 767-15-7, 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. 767-15-7, name is 2-Amino-4,6-dimethylpyrimidine, molecular formula is C6H9N3, 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.

To a solution of 4,6-Dimethyl-pyhmidin-2-ylamine (25 g, 200 mmol) in 400 ml_ of CH2CI2 was added dropwise a solution of hydroxylamine-2,4,6-Trimethyl- benzenesulfonate (105 g, 488 mmol) in 300 ml_ of CH2CI2 at 0°C, and the mixture was stirred at 0°C for 1 hour and filtered. The solid collected was washed with CH2CI2 (100 ml_) to give 1 -Amino-4,6-dimethyl-1 H-pyrimidin-2-ylidene-ammonium 2,4,6-Trimethyl-benzenesulfonate (40 g, yield:62percent).

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 767-15-7, 2-Amino-4,6-dimethylpyrimidine.

Reference:
Patent; H. LUNDBECK A/S; PUeSCHL, Ask; NIELSEN, Jacob; KEHLER, Jan; KILBURN, John, Paul; MARIGO, Mauro; LANGGARD, Morten; WO2011/72694; (2011); A1;,
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Reference of 7627-39-6, 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. 7627-39-6, name is 2,4-Dichloro-5-(ethoxymethyl)pyrimidine. A new synthetic method of this compound is introduced below.

A yellow slurry mixture of (S)-3-hydroxy-10-methyl-9,10,1 1,12-tetrahydro-8H- [1 ,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 NaC1, 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 NaC1 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 NaC1 were charged, maintaining 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 IPA, and dried in a vacuum oven at 40-45 C for 12-16 hours to afford compound? as a yellow solid (41.1 g, 87% yield); HPLC: Waters Ascentis Express C-18 HPLC column, 10 cm X 4.6 tm, 1 mL/min, 234 nm, gradient at 100% 0.1% H3P04 to 100% CH3CN in 10 mm, then hold at 100% CH3CN for 5 mm): tR= 6.40 mm (99.0%). ?H NMR (300 IVIHz, DMSO-d6) 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 (brt, 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); ?3C NMR (75 IVIFIz, DMSO-d6) 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/IVIS m/e=470. Anal. Calcd. for C22H20N503SC1: C, 56.23; H, 4.29; N, 14.90; S, 6.82; Cl, 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; FEIGELSON, Gregg Brian; GEHERTY, Maryll, E.; HEID, JR., Richard Martin; KOTHARE, Mohit; MAN, Hon-Wah; RUCHELMAN, Alexander L.; TRAVERSE, John F.; YONG, Kelvin Hin-Yeong; ZHANG, Chengmin; (123 pag.)WO2018/170203; (2018); A1;,
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