Pyrimidines

Synthetic Route of 56-06-4 ,Some common heterocyclic compound, 56-06-4, molecular formula is C4H6N4O, 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.

Synthesis of Compound (37)Intermediate AA (0.5g, 3.96 mmol) was added to a solution of NaOAc (0.647g, 4.76 mmol, 1.2 eq.) in H20 (15 mL). The reaction was heated to 60 C for ~15 minutes, and a solution of 50% aqueous ClCH2CHO (0.5 mL) was then added. The reaction stirred for 2 hours at 60 C. The reaction mixture was filtered to remove undissolved material, and the filtrate stored at 0 C overnight. The resulting precipitated solid was collected by filtration, washed with cold H20, and dried to obtain Compound (37) (120mg, 20%) as a pink solid. Rf = 0.7 (30%MeOH/CHCl3/0.2 mL of aqueous NH3). 1H-NMR (400MHz, DMSO-_¾ delta 10.95 (br. s, exchanged with D20, 1H), 10.20 (s, exchanged with D20, 1H), 6.60 (dd, J = 3.2, 2.0Hz, 1H), 6.18 (dd, J = 3.2, 2.0Hz, 1H), 6.03 (br. s, exchanged with D20, 2H). Mass (m/z): 150.8 (M++l). LCMS: (Column: Zodiacsil 120-5-C-18-Aq (4.6 * 50 mm), Mobile phase: A: 0.01M HCOONH4 (Aq); B: MeOH, T/%B: 0/5, 10/90, 10.1/5, Flow: 1.0 mL/min, Diluent: MeOH), Rt=2.599 min, 99.16 (214 nm), 99.10 (254 nm).

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. 56-06-4, 2,6-Diaminopyrimidin-4(1H)-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HERCULES TECHNOLOGY MANAGEMENT CO V, INC.; BLAGG, Julian; WO2011/35009; (2011); A1;,
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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 3680-69-1, name is 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. SDS of cas: 3680-69-1

38.4 g (250.4 mmol, 1.0 eq.) with stirring in an ice bath. 4-chloro-7H-pyrrole [2,3-d]pyrimidine is dissolved in 200 mL of dry DMF solution.13 g (305 mmol, 1.2 eq) of 57% NaH was added. The reaction was stirred at room temperature for 1 hour, then 50.9 g of SEMCl (305 mmol, 1.2 eq.).After the addition, the reaction was stirred in an ice bath for 1 hour. quenched with water, extracted with ethyl acetate. the title compound (71 g, yield = 100%) was obtained.

With the rapid development of chemical substances, we look forward to future research findings about 3680-69-1.

Reference:
Patent; Beijing Puqi Pharmaceutical Technology Co., Ltd.; Zhu Li; Hu Wei; Wang Jin; (32 pag.)CN109867675; (2019); A;,
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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.36315-01-2, name is 2-Amino-4,6-dimethoxypyrimidine, molecular formula is C6H9N3O2, molecular weight is 155.16, as common compound, the synthetic route is as follows.Computed Properties of C6H9N3O2

To 50 ml pear-shaped flask add 155 mg (1 mmol) of 2 – amino – 4, 6 – dimethoxy pyrimidine solid and 8 ml of dried DMF, stirring to dissolve adding 2 g water-free K2CO3, Stirring under the room temperature condition 0.5 h, then to slow added in the reaction system of 270 mg (1 mmol) of 5 – bromo valeric acid O-methyl ester, stir at room temperature overnight TLC monitoring to the reaction is complete. After the reaction is finished adding 40 ml of water, then 2 × 50 ml ethyl acetate, the combined organic phase sequentially for 2 × 50 ml of 1 N HCl solution, 2 × 50 ml of saturated sodium chloride solution. The organic phase after drying over anhydrous sodium sulfate the solvent is removed by reduced pressure distillation after purification on silica gel, ethyl acetate/petroleum ether (v/v, 4/1) elution, to obtain light yellow oily liquid, yield 72%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,36315-01-2, 2-Amino-4,6-dimethoxypyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Northwest A&F University; Ji Zhiqin; Wei Shaopeng; (12 pag.)CN107857735; (2018); A;,
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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 916420-27-4, name is tert-Butyl 2,4-dichloro-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate. This compound has unique chemical properties. The synthetic route is as follows. name: tert-Butyl 2,4-dichloro-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate

Step 1- tert-butyl 2-chloro-4-(pyridin-4-yl)-5,6-dihydropyrido[3,4-d]pyrimidine- 7(8H)-carboxylate (ij): 4-(Tributylstannyl)pyridine (247 mg, 0.671 mmol), t-butyl 2,4- dichloro-5,6-dihydropyrido-[3,4-d]pyrimidine-7(8H)-carboxylate (bx) (200 mg, 0.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (76 mg, 0.066 mmol) were dissolved in 1,4- Dioxane (7 mL). The reaction was micro waved at 1300C for 20 minutes The reaction mixture was concentrated on silica gel and purified by flash chromatography (100% Hex to 80% EtOAc/Hex) to give compound ij as a white solid: LC/MS: m/z = + 347.8 (M +H)+.

With the rapid development of chemical substances, we look forward to future research findings about 916420-27-4.

Reference:
Patent; GENENTECH, INC.; BERGERON, Philippe; COHEN, Frederick; ESTRADA, Anthony; KOEHLER, Michael, F. T.; LAU, Kevin, Hon Luen; LY, Cuong; LYSSIKATOS, Joseph, P.; ORTWINE, Daniel, Fred; PEI, Zhonghua; ZHAO, Xianrui; WO2010/14939; (2010); A1;,
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Reference of 171887-03-9, 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 171887-03-9, name is N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 82 25 (20 g, 53 mmol) in 85 n-BuOH (300 mL) was added 86 DIPEA (28 mL) and 90 2-amino-4,6-dichloro-5-formamidopyrimidine (13.2 g, 64 mmol). Resulting mixture was heated in a sealed vessel at 160 C. for 24 h. Volatiles were evaporated, column chromatography (70 AcOEt in 29 toluene 20-100%) afforded title compound (21 g, 75%) as a light yellow solid: 1H NMR (401 MHz, DMSO-d6) delta 8.25 (s, 1H), 6.81 (s, 2H), 4.87 (t, J=5.3 Hz, 1H), 4.74 (q, J=9.5 Hz, 1H), 4.49 (dd, J=9.6, 4.2 Hz, 1H), 4.01 (d, J=4.1 Hz, 1H), 3.57 (ddd, J=11.0, 8.0, 5.2 Hz, 1H), 3.49 (dt, J=11.0, 5.6 Hz, 1H), 2.27 (dt, J=13.4, 9.7 Hz, 1H), 2.11-2.01 (m, 1H), 1.76 (ddd, J=14.0, 9.5, 5.2 Hz, 1H), 0.91 (s, 9H), 0.65 (s, 9H), 0.11 (s, 3H), 0.08 (s, 3H), -0.16 (s, 3H), -0.51 (s, 3H); 13C NMR (101 MHz, DMSO-d6) delta 159.56, 154.42, 149.50, 142.87, 124.09, 75.99, 74.55, 63.22, 58.88, 46.12, 27.71, 26.05, 25.66, 18.01, 17.61, -4.31, -4.42, -5.54; ESI MS m/z (%): 528.3 (100) [M+H], 550.2 (49) [M+Na]; HRMS ESI (C23H43O3N5ClSi2) calculated: 528.25875; found: 528.25868.

According to the analysis of related databases, 171887-03-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY ASCR,V.V.I.; Birkus, Gabriel; Pav, Ondrej; Jandusik, Tomas; Rosenberg, Ivan; Nencka, Radim; US2019/185510; (2019); A1;,
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Application of 2435-50-9, 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. 2435-50-9, name is Pyrimidine-4-carbaldehyde, molecular formula is C5H4N2O, 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.

General procedure: SI, Figure 4. General procedure of the reductive amination reactions: synthesis of AA9-AA24 compounds (Tables 1 and 2). The ethyl 3-amino-4-(cyclohexylamino)benzoate (AA1) and derivatives (1 equiv.)and benzaldehyde (1 equiv) were heated in DCE for 1h at 80 oC in the presence of molecular sieves (4 A), then the mixture was cooled down to room temperature before addition of the NaBH(OAc)3 (1.6 equiv.) in small portions over 3h. The reaction mixture was stirred at room temperature under a nitrogen atmosphere for 17h. The reaction mixture was quenched with aqueous saturated NaHCO3, and the product was extracted with EtOAc. The EtOAc extract was dried (MgSO4), and the solvent was evaporated. The residue was purified by flash-column chromatography on silica gel, using a mixture of solvent of DCM: MeOH (50:1), to provide the desired AA9-AA24 compounds (Tables 1-2).

According to the analysis of related databases, 2435-50-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Iniguez, Eva A.; Perez, Andrea; Maldonado, Rosa A.; Skouta, Rachid; Bioorganic and Medicinal Chemistry Letters; vol. 25; 22; (2015); p. 5315 – 5320;,
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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. 5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

To a solution of 4-chloro-1H-pyrazolo[3,4-d]pyrimidine 2 (0.1 g, 0.65 mmol) in anhydrous DMF(5 mL ), TEA (0.22 g, 0.65 mmol) was firstly added and stirred at room temperature for 30 min. Then, asolution of benzyl bromide (0.11 g, 0.78 mmol) in anhydrous DMF (5 mL) was added and the mixturewas reacted for 1 h, then KI was added and continue reaction. The reaction mixture was at last dilutedwith water (15 mL), and extracted with ethyl acetate. The organic layer was washed with water andthe organic phase was dried over MgSO4 and concentrated, and the residue was purified by columnchromatography on silica gel using 10:1 petroleum ether/ethyl acetate as eluent to give 6: 65% yield,mp 62-63 C; 1H-NMR (400 MHz, DMSO-d6) delta: 8.91 (s, 1H, CH), 8.53 (s, 1H, CH), 7.26-7.33 (m, 5H,ArH), 5.70 (s, 2H, CH2); 13C-NMR (100 MHz, DMSO-d6) 156.6, 151.3, 150.9, 137.2, 135.1, 129.0, 129.0,128.1, 128.1, 128.0, 106.3, 50.8; IR (KBr, delta, cm-1): 3441, 3090, 2935, 1897, 1756, 1585, 1547, 1479, 1410,1347, 1243, 1174, 1135, 950, 858, 783, 730, 698, 596, 534; HRMS (ESI) calcd. for C12H10ClN4: [M + H]+245.0594, found 245.0584.

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, 5399-92-8, 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine.

Reference:
Article; Li, Yong; Cao, Ting-Ting; Guo, Shanchun; Zhong, Qiu; Li, Cai-Hu; Li, Ying; Dong, Lin; Zheng, Shilong; Wang, Guangdi; Yin, Shu-Fan; Molecules; vol. 21; 6; (2016);,
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Electric Literature of 1208901-69-2, 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 1208901-69-2, name is 2,4-Dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine hydrochloride. This compound has unique chemical properties. The synthetic route is as follows.

[0076] To the mixture of 2,4-dichloro-5 ,6,7, 8-tetrahydropyrido[4,3 -d]pyrimidine (2.20 g, 9.15 mmol, HC1 salt) in CH2C12 (30.00 mL) was added dropwise TEA (2.78 g, 27.45 mmol, 3.81 mL) at 0 C. Then the mixture was stirred under N2 at 0 C for 5 mm. To the mixture was added 2-methylpropanoyl chloride (1.17 g, 10.98 mmol, 1.15 mL) at 0 C. The mixture was stirred under N2 at 0 C for 2 h. LCMS showed one main peak of desired product. TLC (petroleum ether/EtOAc=1:1, Rf=0.6) showed one new main spot. The mixture was diluted with CH2C12 (40 mL) and washed with water (40 mLx2), citric acid (10%, 40 mLx3), sat.NaHCO3 (40 mLx2), brine (40 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to afford the title compund (2.50 g, crude) as a light yellow solid which was used in the next step without further purification. ?H NIVIR (400 IVIHz, DMSO-d6) oe 4.67-4.59 (m, 2H), 3.85-3.79 (m, 2H), 3.03-2.99 (m, 2H), 2.89-2.85 (m, 1H), 1.04 (d, J 6.4 Hz, 6H).

According to the analysis of related databases, 1208901-69-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KADMON CORPORATION, LLC; OLSZEWSKI, Kellen; POYUROVSKY, Masha; BARSOTTI, Anthony; KIM, Ji-In; LIU, Kevin; MORRIS, Koi; (143 pag.)WO2016/210331; (2016); A1;,
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Related Products of 22536-61-4, 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.22536-61-4, name is 2-Chloro-5-methylpyrimidine, molecular formula is C5H5ClN2, molecular weight is 128.56, as common compound, the synthetic route is as follows.

A solution of 2- chloro-5-methylpyrimidine (500 g, 3889 mmol, 1.0 equiv.) in DMF (5 L) was degassed with N2 for 20 min and dppf (108 g, 194 mmol, 0.05 equiv.) and Pd2(dba)3 (178 g, 194 mmol, 0.05 equiv.) were added to the reaction mixture. Zn(CN)2(685 g, 5834 mmol, 1.5 equiv.) was then added, and the reaction mixture was heated at 100 C for 16h. The reaction was quenched with water (5 L) and stirred for 10 min. The reaction mixture was then filtered through a pad of Celite brand filter agent. The filtrate was diluted with water (4 L) and extracted with EtOAc (2 x 4 L). The combined organic layers were washed with brine (4 L), dried over Na2SO4,filtered and concentrated under reduced pressure to give the initial product which was further purified by column chromatography using silica gel (60-120 mesh) and 0-10 % EtOAc in hexanes to obtain Example 468.1 (330 g, 71 %) as an off white solid.1H NMR (400 MHz, DMSO-d6) delta 8.89 (s, 2H), 2.39 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 22536-61-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YANG, Kevin; YEH, Wen-Chen; (700 pag.)WO2018/97945; (2018); A1;,
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Reference of 1142188-60-0, 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 1142188-60-0 as follows.

To a solution of tert-butyl 4-hydroxy-6,8-dihydro-5H-pyrido[3,4-d] pyrimidine-7-carboxylate (16.0 g, 63.7 mmol, 1.00 eq) in DMF (4.00 mL) was added DBU (29.1 g, 191 mmol, 28.8 mL, 3.00 eq) and benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PYBOP) (39.8 g, 76.4 mmol, 1.20 eq). The mixture was stirred at 25° C. for 1 hour. Benzyl piperazine-1-carboxylate (21.0 g, 95.5 mmol, 18.5 mL, 1.50 eq) was added and the reaction mixture was stirred at 25° C. for 16 hours. The mixture was diluted with ethyl acetate (500 mL) and washed with water (3 400 mL), dried over Na 2SO 4, filtered and concentrated under vacuum. The residue was purified by column chromatography (SiO 2, diethyl ether/ethyl acetate=1:1) to give tert-butyl 4-(4-benzyloxycarbonylpiperazin-1-yl)-6,8-dihydro-5H-pyrido[3,4-d]pyrimid- ine-7-carboxylate (2.00 g, 4.41 mmol, 6.93% yield) as a yellow oil. ESI MS m/z 454.3 [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,1142188-60-0, its application will become more common.

Reference:
Patent; Mirati Therapeutics, Inc.; Array BioPharma Inc.; Blake, James F.; Burgess, Laurence E.; Chicarelli, Mark Joseph; Christensen, James Gail; Cook, Adam; Fell, Jay Bradford; Fischer, John P.; Marx, Matthew Arnold; Mejia, Macedonio J.; Savechenkov, Pavel; Vigers, Guy P.A.; Smith, Christopher Ronald; Rodriguez, Martha E.; US2019/144444; (2019); A1;,
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