Tag: M.W:100-200

Electric Literature of 504-17-6, 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.504-17-6, name is 4,6-Dihydroxy-2-mercaptopyrimidine, molecular formula is C4H4N2O2S, molecular weight is 144.1518, as common compound, the synthetic route is as follows.

General procedure: A mixture of dimedone (0.140 g, 1 mmol), isatin (0.147 g, 1 mmol) and malononitrile (0.066 g, 1 mmol) was stirred in round bottom flask containing 5 mL of oxalic acid dihydrate:proline LTTM at room temperature for an appropriate time. After completion of the reaction, as indicated by TLC, 10 mL of water was added to the reaction mixture and the insoluble crude product was filtered off. The aqueous layer was evaporatedunder vacuumto recover the LTTM. The crude product was washed with distilled water(5 mL) and recrystallized from ethanol (10 mL).

Statistics shows that 504-17-6 is playing an increasingly important role. we look forward to future research findings about 4,6-Dihydroxy-2-mercaptopyrimidine.

Reference:
Article; Chandam, Dattatray R.; Mulik, Abhijeet G.; Patil, Dayanand R.; Deshmukh, Madhukar B.; Research on Chemical Intermediates; vol. 42; 2; (2016); p. 1411 – 1423;,
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.74356-36-8, name is 2,4-Dimethyl-pyrimidine-5-carboxylic acid, molecular formula is C7H8N2O2, molecular weight is 152.1506, as common compound, the synthetic route is as follows.Quality Control of 2,4-Dimethyl-pyrimidine-5-carboxylic acid

110 mg (0.72 mmol) of 2,4-dimethyl-pyrimidine-5-carboxylic acid and 215 mg (0.57 mmol) of O-(benzotriazol-1-yl)N,N,N’,N’-tetramethyluronium-hexa-fluorophosphate are dissolved in 4 mL of N,N-dimethylformamide and 62 muL (0.57 mmol) of 4-methyl-morpholine are added. The mixture is stirred for 10 min and a solution of 170 mg (0.47 mmol) [(R)-1-piperidin-4-yl-2-(2,4,5-trifluoro-phenyl)-ethyl]-carbamic acid tert-butyl ester and 102 muL (0.57 mmol) of di-iso-propylethylamine in 4 mL of N,N-dimethylformamide is added. The reaction mixture is stirred for 2 h at room temperature, and diluted with ethyl acetate. The organic layer is washed with brine, saturated sodium bicarbonate solution and brine, dried with sodium sulfate, filtered and concentrated in vacuo to yield the title compound. LC/MS (I) (5-95%, 5 min): rt 3.89 min; m/z 437, 493 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,74356-36-8, 2,4-Dimethyl-pyrimidine-5-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Santhera Pharmaceuticals (Schweiz) AG; BIOVITRUM AB; EP2019099; (2009); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3764-01-0, 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. 3764-01-0, name is 2,4,6-Trichloropyrimidine, molecular formula is C4HCl3N2, 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.

A solution of iotaetaomicronphietaomicronetabeta (100 g; 1.15 moles; 5.3 equivalents) in THF (450 mL) was cooled with an ice bath. A solution of 2,4,6-trichloropyrimidine (39.9 g; 217 mmoles; 1.0 equivalents) in THF (100 mL) was added over a period of 30 minutes. A copious white precipitate formed upon addition of 2,4,6-trichloropyrimidine and the reaction mixture rapidly thickened. The mixture was allowed to warm to ambient temperature and mechanically stirred for 64 hours (heating the reaction mixture at reflux following the addition of 2,4,6-trichloropyrimidine leads to complete reaction in 60 min. The ratio of a to b was unchanged). The mixture was then filtered and the filter cake washed with additional THF (2 x 100 mL). The filtrate was concentrated on the rotavap. Water (600 mL) was added and the resulting slurry was stirred for 30 minutes. The solids were isolated by filtration, washed with additional water (2 x 100 mL) and dried overnight under vacuum. Yield a + b: 61.3 g (99%). Product was 87% a by hplc area percent; remainder is b.[00128] 31 g of the crude solid was dissolved in 200 mL of CH2CI2 and applied to 600 g of dry silica in a fritted glass funnel. The silica was eluted with 1 : 1 hexane : EtOAc and 300 mL fractions were collected. TLC analysis shows a to be present in fractions 1 -7 and 4,6- dimo holino-2-chloropyrimidine in fractions 6-10. Fractions 1-5 were pooled and concentrated to provide a white solid. Yield: 28.2 g (Product was 98% a by hplc area percent).

According to the analysis of related databases, 3764-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; ZHAO, Jean J.; WANG, Qi; WO2012/109423; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 14394-70-8, 2-Chloro-5-methylpyrimidin-4-amine, 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, 14394-70-8, blongs to pyrimidines compound. Formula: C5H6ClN3

[0293] A mixture of l-bromo-3,5-dimethoxybenzene (436 mg, 2.01 mmol), 2-chloro~5- methyl-pyrimidin-4-ylamine (287 mg, 2.00 mmol), Pd(OAc)2 (44 mg, 0.20 mmol), Xantphos (237 mg, 0.41 mmol) and potassium fe/t-butoxide (448 mg, 3.99 mmol) in dioxane (15 mL) and DMF (5 mL) was microwaved at 160 C for 20 min. The reaction mixture was cooled to room temperature and filtered rinsing with DCM and methanol. The filtrate was concentrated and purified using gradient flash chromatography (0-100% ethyl acetate in hexanes) to afford the title compound as a yellow solid (182 mg, 33%).[0294] 1H NMR (500 MHz, DMSO-d6): delta 2.17 (s, 3H), 3.74 (s, 6H), 6.27 (t, J= 2.2 Hz, IH), 6.99 (d, J=2.2 Hz, 2H), 8.06 (s, IH), 8.71 (s, IH). MS (ES+): m/z 280 (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,14394-70-8, its application will become more common.

Reference:
Patent; TARGEGEN, INC.; WO2007/53452; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 149849-92-3 ,Some common heterocyclic compound, 149849-92-3, molecular formula is C5H3ClN2O2, 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 suspension of 2-chloropyrimindine-4-carboxylic acid (500 mg, 3.15 mmol) and DMF(0.024 mL, 0.32 mmol) in DCM (30 mL) stirred under nitrogen at 0 C was added a 2 Msolution of oxalyl chloride (1.74 mL, 3.47 mmol) in DCM dropwise. The reaction minxturewas allowed to warm to rt and stirred for further 3 h at rt. The reaction minxture wasevaporated in vacuo to give a brown oil. This residue was dissolved in THF (20 mL) and MeOH was added (0.14 mL, 3.5 mmol) dropwise. The reaction minxture was stirred at rt under nitrogen for lh. The reaction minxture was evaporated in vacuo to afford methyl 2- chloropyrimindine-4-carboxylate (780 mg, 4.5 mmol, purity: 80 %, recovery: 143 %) as abrown oil. The compound was used in the next step without purification. LCMS (mlz) 173 and 175 (M+H), retention time: 1.86 mm, LC/MS Method 2.

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. 149849-92-3, 2-Chloropyrimidine-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DAUGAN, Alain Claude-Marie; DONCHE, Frederic G.; FAUCHER, Nicolas Eric; GEORGE, Nicolas S.; (243 pag.)WO2018/92089; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5177-27-5, 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 5177-27-5, name is 5-Amino-2,4-dichloropyrimidine. This compound has unique chemical properties. The synthetic route is as follows.

Tri(2-furyl)phosphine (36 mg, 0.16 mmol) and Pd2(dba)3 (20 mg, 0.020 mmol) were added to DMF (10 mL) under N2 at ambient temperature and stirred for 10 min. Subsequently, 2,4-dichloropyrimidine-5-amine (8d) (100 mg, 0.600 mmol) and (2-furyl)tributyltin (0.2 mL, 0.6 mmol) were added. The mixture was stirred at 60 C for 16 h, and evaporated in vacuo. The residue was dissolved in satd KF in THF (20 mL), stirred at ambient temperature for 16 h, and evaporated in vacuo. The residue was placed on top of a flash chromatography column and the product was purified by flash chromatography on silica gel eluting with EtOAc/CH2Cl2/hexane (5:8:12); yield 73 mg (61%), mp 169-170 C, yellow solid. 1H NMR (CDCl3, 500 MHz) delta 8.08 (s, 1H, H-4), 7.61 (dd, J=1.8, 0.7 Hz, 1H, H-5 in furyl), 7.31 (dd, J=3.6, 0.7 Hz, 1H, H-3 in furyl), 6.59 (dd, J=3.6, 1.8 Hz, 1H, H-4 in furyl), 4.71 (s, 2H, NH2); 13C NMR (CDCl3, 75 MHz) delta 152.4 (C-2 in furyl), 149.6 (C-2), 148.2 (C-4), 144.6 (C-5 in furyl), 141.3 (C-6), 135.1 (C-1), 113.9 (C-3 in furyl), 112.8 (C-4 in furyl); MS EI m/z (rel %) 197/195 (38/100, M+), 168 (19), 166 (49), 67 (3); HRMS (EI) calcd for C8H6ClN3O: 195.0199. Found 195.0197.

According to the analysis of related databases, 5177-27-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Read, Matthew L.; Krapp, Andreas; Miranda, Pedro O.; Gundersen, Lise-Lotte; Tetrahedron; vol. 68; 7; (2012); p. 1869 – 1885;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 89487-99-0, 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.89487-99-0, name is 4-Hydroxy-2-(methylthio)pyrimidine-5-carbonitrile, molecular formula is C6H5N3OS, molecular weight is 167.19, as common compound, the synthetic route is as follows.

4-Hydroxy-2-(methylthio) pyrimidine-5-carbonitrile (3 mmol) and m-anisidine (3 mmol) in pentan-1-ol was refluxed for 40 h under nitrogen. The reaction mixture was concentrated in vacuo. The residue was washed with water and dried to afford 4-hydroxy-2-(3-methoxyphenylamino)pyrimidine-5-carbonitrile.

Statistics shows that 89487-99-0 is playing an increasingly important role. we look forward to future research findings about 4-Hydroxy-2-(methylthio)pyrimidine-5-carbonitrile.

Reference:
Patent; Hutchison MediPharma Enterprises Limeted; US2008/255172; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 3435-28-7 ,Some common heterocyclic compound, 3435-28-7, molecular formula is C5H7N3, 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 Example 154a (100 mg, 0.26 mmol,) and Example 154b (45 mg, 0.39 mmol) in DMA (2.5 mL) were added Pd2(dba)3 (24 mg, 0.026 mmol), Xantphos (30 mg, 0.052 mmol) and Cs2CO3 (340 mg, 1.04 mmol). The mixture was degassed by nitrogen for 3 times and stirred at 130oC for 2 h. When completed, the reaction was cooled to r.t., diluted with MeOH (5 mL) and filtered. The filtrate was purified directly by Prep-HPLC to give the desired product Example 154 (40.0 mg, 34.2% yield) as a white solid. LCMS [M+1] + = 457.2.1H NMR (400 MHz, DMSO-d6) d 11.03 (s, 1H), 10.27 (s, 1H), 9.14 (s, 1H), 8.55 (s, 2H), 7.78 (s, 1H), 7.65-7.57 (m,3H), 7.30 (d, J = 7.9 Hz, 1H), 3.93 (s, 3H), 3.69 (s, 3H), 2.97 (s, 1H), 2.34 (s, 3H), 1.07 (s, 2H), 1.01 (s 2H).

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. 3435-28-7, 6-Methylpyrimidin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; KALDOR, Stephen W.; (0 pag.)WO2020/86616; (2020); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Application of 29274-24-6 ,Some common heterocyclic compound, 29274-24-6, molecular formula is C6H4ClN3, 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.

General Procedure 32-Methyl-4-pyrazolo[1 ,5-a]pyrimidin-5-yl-but-3-yn-2-ol (5a); [00151] Compound 1a, 2-methyl-but-3-yn-2-ol (1.5 equivalents), Pd CI2[PPh3]2 (5 mol %) and CuI (10 mol %) in diethyl amine is refluxed under argon for 2 h (TLC control), then cooled and evaporated to dryness. The residue is dissolved in dichloromethane; the target product is isolated by column chromatography (silica gel, ethyl acetate – hexane, 1 :2). The solvent is evaporated under reduced pressure; the residue is crystallized from diethyl ether to give the title compound in good yield.1H NMR (DMSO-d6, 400 MHz) delta (ppm), 1.51 (s, 6H), 6.69 (s, 1 H), 6.98 (d, 1 H), 8.22 (s.1 H)1 9.06 (d, 1 H). m/z (APCI+) 202 (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,29274-24-6, its application will become more common.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGaA; HENRICH, Markus; WEIL, Tanja; NAGEL, Jens; GRAVIUS, Andreas; MUeLLER, Sibylle; KAUSS, Valerjans; ZEMRIBO, Ronalds; FOTINS, Juris; WO2010/63487; (2010); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5177-27-5, 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. 5177-27-5, name is 5-Amino-2,4-dichloropyrimidine, molecular formula is C4H3Cl2N3, 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.

A mixture of 2,4-dichloropyrimidin-5-amine (0.5 g, 3.04 mmol), sodium methoxide (0.66 g, 12.19 mmol) and methanol (10 ml) was refluxed for 16 hours. The solvent was removed under reduced pressure. Water was added and the aqueous phase was extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 2-chloro-4-methoxypyrimidin-5-amine after flash chromatography (100-200 mesh size silica gel, 20-25% ethyl acetate in hexane) was 0.35 g. N-Bromosuccinimide (67 mg, 0.37 mmol) was added to a solution of 2-chloro-4-methoxypyrimidin-5-amine (50 mg, 0.31 mmol) in chloroform (2 ml) and the resulting mixture was stirred at RT for 3 hours. Water was added and the mixture extracted with chloroform. The organic phase was washed with water and brine, dried over sodium sulphate and concentrated under reduced pressure. The yield of 4-bromo-2-chloro-6-methoxypyrimidin-5-amine was 60 mg.

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 5177-27-5, 5-Amino-2,4-dichloropyrimidine.

Reference:
Patent; MEDEIA THERAPEUTICS LTD; RATILAINEN, Jari; GOLDSTEINS, Gundars; WO2014/191632; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia