Category: 99586-66-0

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. 99586-66-0, name is 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows. category: pyrimidines

(S)-1-(6-(1-(Difiuoromethyl)-1H-pyrazol-5-yl)-1-methyl-1H-pyrrolo[3,2-b]pyridin- 5-yl)ethanamine (115 mg, 0.393 mmol), 2-amino-4-chloro-6-methylpyrimidine-5-carbonitrile (100 mg, 0.593 mmol), and N-ethyl-N-isopropylpropan-2-amine (0.21 mL, 1.2 mmol) were combined in acetonitrile (6 mL). The reaction mixture was heated in a microwave reactor at 120C for 2 hours and then concentrated. The residue was taken up in DMF and purified by preparative HPLC (basic mode) eluting with 30-45% ACN in water. The fractions containing the desired compound were combined and extracted with EtOAc (200 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound (97 mg, 58%). 1H NMR (500 MHz, CD3OD) delta ppm 1.41 – 1.49 (m, 3 H), 3.88 (s, 3 H), 5.91 (q, J=6.67 Hz, 1 H), 6.63 (d, J=2.93 Hz, 1 H), 6.86 (d, J=2.44 Hz, 1 H), 7.49 – 7.77 (m, 2 H), 7.95 (s, 1 H), 8.19 (d, J=2.93 Hz, 1 H); ESI-MS m/z [M+H]+ calc’d for C19H18F2N10, 425; found 425.

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Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; CHANG, Edcon; NOTZ, Wolfgang Reinhard Ludwig; WALLACE, Michael B.; WO2014/11568; (2014); A1;,
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Pyrimidine – Wikipedia

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. 99586-66-0, name is 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile, molecular formula is C6H5ClN4, 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. Formula: C6H5ClN4

The procedure mentioned in Scheme 6 was used with compound 1.31 (32.0 mg, 0.058 mmol) and trifluoroacetic acid (133.0 mg, 1.17 mmol, 89.0 pi) in DCM (0.6 ml). The resulting mixture was stirred at room temperature for 3 hours and worked-up (Method B) to afford methyl (S )-3 -(1 -(2-( 1 -aminopropyl)-4-oxo-3 -phenyl-3 ,4-dihydroquinazolin-5- yl)piperidin-4-yl)propanoate 6.1f. The free amine 6.1f was used with 2-amino-4-chloro-6- methylpyrimidine-5-carbonitrile (15.0 mg, 0.09 mmol) and DIPEA (22.0 mg, 0.17 mmol, 30.0 pi) in n-butanol (0.3 ml) and heated at 130 C for 2 hours. The remaining residue was purified by flash chromatography on silica gel using 0-100% EtOAc/hexanes to afford the product methyl (S )-3 -(1 -(2-( 1 -((2-amino-5-cyano-6-methylpyrimidin-4-yl)amino)propyl)-4- oxo-3 -phenyl-3 ,4-dihydroquinazolin-5-yl)piperidin-4-yl)propanoate 6.2n (21.0 mg, 0.04 mmol) in 63% yield. LC-MS (method 1): tR = 2.61 mi mlz (M+H) = 581.3.

With the rapid development of chemical substances, we look forward to future research findings about 99586-66-0.

Reference:
Patent; THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; GREWAL, Gurmit; THAKUR, Ashish; TAWA, Gregory James; FERRER, Marc; SIMEONOV, Anton M.; (191 pag.)WO2018/237007; (2018); 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. 99586-66-0, name is 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile

General procedure: To a solution of 7a (80mg, 0.18mmol, 1 equiv), 4-amino-6-chloropyrimidine-5-carbonitrile (31mg, 0.2mmol, 1.1 equiv) in BuOH was added DIPEA (0.06mL, 0.36mmol, 2 equiv). The mixture was reacted under microwave at 130C for 20min. After completion, the solvent was removed under reduced pressure. The residue was redissolved in CH2Cl2. The crude was further purified via silica gel chromatography to give compound 8a as white solid (81mg, 80%).

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, 99586-66-0, 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile.

Reference:
Article; Wei, Manman; Zhang, Xi; Wang, Xiang; Song, Zilan; Ding, Jian; Meng, Ling-Hua; Zhang, Ao; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 1156 – 1171;,
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Application of 99586-66-0, 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.99586-66-0, name is 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile, molecular formula is C6H5ClN4, molecular weight is 168.58, as common compound, the synthetic route is as follows.

The procedure mentioned in Scheme 6 was used with compound 1.3h (45.0 mg, 0.084 mmol) and trifluoroacetic acid (192.0 mg, 1.68 mmol, 0.13 ml) in DCM (0.8 ml). The resulting mixture was stirred at room temperature for 3 hours and worked-up (Method B) to afford methyl (S )-2-( 1 -(2-( 1 -aminopropyl)-4-oxo-3 -phenyl-3 ,4-dihydroquinazolin-5- yl)piperidin-4-yl)acetate 6.le. The free amine 6.le was used with 2-amino-4-chloro-6- methylpyrimidine-5-carbonitrile (21.0 mg, 0.13 mmol) and DIPEA (33.0 mg, 0.25 mmol, 44.0 pi) in n-butanol (0.3 ml) and heated at 130 C for 2 hours. The remaining residue was purified by flash chromatography on silica gel using 0-100% EtOAc/hexanes to afford the product methyl (S )-2-( 1 -(2-( 1 -((2-amino-5-cyano-6-methylpyrimidin-4-yl)amino)propyl)-4- oxo-3 -phenyl-3 ,4-dihydroquinazolin-5-yl)piperidin-4-yl)acetate 6.2m (34.0 mg, 0.06 mmol) in 71% yield. LC-MS (method 1): tR = 2.57 mi mlz (M+H) = 567.3.

Statistics shows that 99586-66-0 is playing an increasingly important role. we look forward to future research findings about 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile.

Reference:
Patent; THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; GREWAL, Gurmit; THAKUR, Ashish; TAWA, Gregory James; FERRER, Marc; SIMEONOV, Anton M.; (191 pag.)WO2018/237007; (2018); A1;,
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Pyrimidine – Wikipedia

Adding a certain compound to certain chemical reactions, such as: 99586-66-0, 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile, 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, Recommanded Product: 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile, blongs to pyrimidines compound. Recommanded Product: 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile

The procedure mentioned in Scheme 6 was used with (S)-methyl 6-((2-(1- ((tert-butoxycarbonyl)amino)propyl)-4-oxo-3 -phenyl-3 ,4-dihydroquinazolin-5- yl)amino)hexanoate 1.3b (110.0 mg, 0.21 mmol) and trifluoroacetic acid (480.0 mg, 4.21 mmol, 0.32 ml) in dichioromethane (2.1 ml). The resulting mixture was stirred at room temperature for 3 hours and worked-up (Method A) to form (S)-methyl 6-((2-(1- aminopropyl)-4-oxo-3 -phenyl-3 ,4-dihydroquinazolin-5-yl)amino)hexanoate 6.11. This free amine 6.11 was used with 2-amino-4-chloro-6-methylpyrimidine-5-carbonitrile (53.0 mg, 0.32 mmol) and diisopropylethylaime (81.0 mg, 0.63 mmol, 110.0 pi) in n-butanol (0.5 ml) and heated at 130 C for 2 hours. The remaining residue was purified by flash chromatography on silica gel using 0-100% EtOAc/Hexanes to afford the product methyl (5)- 6-((2-(1-((2-amino-5-cyano-6-methylpyrimidin-4-yl)amino)propyl)-4-oxo-3-phenyl-3,4- dihydroquinazolin-5-yl)amino)hexanoate 6.2q (97.0 mg, 0.174 mmol) in 83% yield. LC-MS (method 1): tR = 3.25 mi mlz (M + H)+ = 555.3.

The synthetic route of 99586-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; GREWAL, Gurmit; THAKUR, Ashish; TAWA, Gregory James; FERRER, Marc; SIMEONOV, Anton M.; (191 pag.)WO2018/237007; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 99586-66-0 ,Some common heterocyclic compound, 99586-66-0, molecular formula is C6H5ClN4, 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.

In this example, two different synthesis reactions were performed subsequently in one reaction vessel without exchange of the reaction medium. (0077) 5.0 g (1 1 .3 mmol) of 5-bromo-6-fluoro-2-((2S,4S)-4-hydroxypyrrolidin-2-yl)-3- phenylquinazolin-4(3/-/)-one hydrochloride and 1 .9 g (12.5 mmol / 1 .1 eq.) of (2- methoxypyrimidin-5-yl)boronic acid was provided in a reaction mixture comprising 5.0 mol% PdCI2(dtbpf) and 3.0 eq. NMM in 40 ml (8V) 2% TPGS-750-M in water and 20 ml (4V) THF. The reaction mixture formed a stable emulsion and the reaction was allowed to proceed for 16 h at 50C under stirring. Then 1 .7 g (10.2 mmol / 0.9 eq.) of 2-amino- 4-chloro-6-methylpyrimidine-5-carbonitrile in 10 ml (2V) THF were added to the reaction mixture. After 18 h at room temperature the product 2-amino-4-((2S,4S)-2-(6- fluoro-5-(2-methoxypyrimidin-5-yl)-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)-4- hydroxypyrrolidin-1 -yl)-6-methylpyrimidine-5-carbonitrile was obtained. (0078) (0079) The same reaction performed in conventional organic solvent (e.g. N- methylpyrrolidone) resulted in about 30% side product (structure in bracket) of the Suzuki cross-coupling reaction. This could be reduced to 3% with the use of 2% TPGS- 750-M in water as solvent and THF as co-solvent.

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. 99586-66-0, 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; GALLOU, Fabrice; PARMENTIER, Michael; ZHOU, Jianguang; GUO, Pengfei; (27 pag.)WO2017/168303; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 99586-66-0 ,Some common heterocyclic compound, 99586-66-0, molecular formula is C6H5ClN4, 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: d) At rt, a solution of intermediate Xl (1 eq.) and an aryl halogenide VIII (1 to 2.5 eq.) in alcohol (nBuOH or EtOH, 0.08M to 0.1M) was treated with DIPEA (2 to Seq.) and irridiated in a microwave reactor or heated in an oil bath at 120-160C for 0.5 h to 6 d. Purification of intermediates and final products IX was carried out by flash chromatography,HPLCorSFC.

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. 99586-66-0, 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; DU, Zhenxing; HINTERMANN, Samuel; HURTH, Konstanze; JACQUIER, Sebastien; LEHMANN, Hansjoerg; MOEBITZ, Henrik; SOLDERMANN, Nicolas; STOJANOVIC, Aleksandar; WO2015/10641; (2015); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 99586-66-0, Adding some certain compound to certain chemical reactions, such as: 99586-66-0, name is 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile,molecular formula is C6H5ClN4, 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 99586-66-0.

General procedure: To a solution of 7a (80mg, 0.18mmol, 1 equiv), 4-amino-6-chloropyrimidine-5-carbonitrile (31mg, 0.2mmol, 1.1 equiv) in BuOH was added DIPEA (0.06mL, 0.36mmol, 2 equiv). The mixture was reacted under microwave at 130C for 20min. After completion, the solvent was removed under reduced pressure. The residue was redissolved in CH2Cl2. The crude was further purified via silica gel chromatography to give compound 8a as white solid (81mg, 80%).

According to the analysis of related databases, 99586-66-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wei, Manman; Zhang, Xi; Wang, Xiang; Song, Zilan; Ding, Jian; Meng, Ling-Hua; Zhang, Ao; European Journal of Medicinal Chemistry; vol. 125; (2017); p. 1156 – 1171;,
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. 99586-66-0, name is 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile, the common compound, a new synthetic route is introduced below. Quality Control of 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile

d) 2-Am ino-4-((2S,4S)-4-hydroxy-2-(4-oxo-3-phenyl-5-(trifluoromethyl)-3,4- dihydroquinazolin-2-yI)pyrrolidin-1 -yI)-6-methylpyrimidine-5-carbonitrile A solution of 2-((2S,4S)-4-hydroxypyrrolidin-2-yl)-3-phenyl-5-trifluoromethyl)qu inazolin-4(3H)-one (290 mg, 0.77 mmol) and 2-amino-4-chloro-6-methylpyrimidine-5-carbonitrile (CAS registry 99586-66-0) (130 mg, 0.77 mmol) in nBuOH (7.7 ml) was treated with DIPEA (0.540 ml, 3.09 mmol) and was stirred at 90C for 18 h in an oil bath. The reaction mixture was cooled down, and evaporated under reduced pressure. The oil was taken up in DCM and washed with water, the organic layer was dried over MgSO4 and concentrated in vacuo (500mg). The crude was purified over SFC (column NH2, 250 x 30 mm, 60A, 5pm, Princeton, flow at 100 mI/mm; gradient of MeCH in supercritical CC2, from 17% to 22% in ii mm) and triturated with pentane to afford the title compound as a beige solid (258 mg, 66% yield).HPLC RtM2=0.94 mm; ESIMS: 508 [(M+H)].1H NMR (400 MHz, DMSO-d6): O 7.98 – 7.80 (m, 4H), 7.65-7.47 (m, 4H), 7.13-6.52 (m, 2H),5.25 (brs, 1H), 4.65 (brs, 1H), 4.17 (d, 2H), 3.79-3.60 (m, 1H), 2.27 (5, 3H), 2.07-1.96 (m,1H), 1.96-1.84 (m, 1H).

The synthetic route of 99586-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; GUIBOURDENCHE, Christel; HINTERMANN, Samuel; HURTH, Konstanze; JACQUIER, Sebastien; KALIS, Christoph; MOEBITZ, Henrik; SOLDERMANN, Nicolas; WO2014/128612; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia