Category: 5399-92-8

Synthetic Route of 5399-92-8, 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. 5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below.

EXAMPLE 107; 4-(7-(benzyloxy)-lH-benzordlimidazol-2-yl)-l-(lH-pyrazolor3,4-dlpyrimidin-4- yl)piperidin-4-amine107 A. Methyl 4-(tert-butoxycarbonylamino)-l-(lH-pyrazolor3,4-dlpyrimidin-4- yl)piperidine-4-carboxylateTriethylamine (25.3 mL, 181.81 mmol) was added in one portion to a stirred suspension of methyl 4-(t°t-butoxycarbonylamino)piperidine-4-carboxylate (10.80 g, 41.82 mmol) and 4-chloro-lH-pyrazolo[3,4-d]pyrimidine (5.62 g, 36.36 mmol)** in ethanol (175 mL) at 2O0C under nitrogen. The resulting solution was stirred at 2O0C for 30 minutes and at 5O0C for 10 minutes. The solution was filtered and the filtrate was evaporated. The crude product was purified by flash silica chromatography, elution gradient 2 to 8% MeOH in DCM. Pure fractions were evaporated to dryness to afford methyl 4-(tert- butoxycarbonylamino)- 1 -( 1 H-pyrazo Io [3 ,4-d]pyrimidin-4-yl)piperidine-4-carboxylate (9.94 g, 72.6 %) as a cream dry film, m/z (ESI+) M+ = 377; HPLC tR = 1.24 min; IH NMR (399.9 MHz, DMSO-d6) delta 1.41 (9H, s), 1.92 – 1.97 (2H, m), 2.07 – 2.10 (2H, m), 3.57 (2H, m), 3.63 (3H, s), 4.34 (IH, s), 7.53 (IH, s), 8.24 (IH, s), 8.30 (IH, s), 13.52 (IH, s).H= * Commercially available from Chontech (catalogue number: 07044)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5399-92-8, 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH:ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; ASTRAZENECA AB; WO2008/75109; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5399-92-8, 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. 5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below.

EXAMPLE 107; 4-(7-(benzyloxy)-lH-benzordlimidazol-2-yl)-l-(lH-pyrazolor3,4-dlpyrimidin-4- yl)piperidin-4-amine107 A. Methyl 4-(tert-butoxycarbonylamino)-l-(lH-pyrazolor3,4-dlpyrimidin-4- yl)piperidine-4-carboxylateTriethylamine (25.3 mL, 181.81 mmol) was added in one portion to a stirred suspension of methyl 4-(t°t-butoxycarbonylamino)piperidine-4-carboxylate (10.80 g, 41.82 mmol) and 4-chloro-lH-pyrazolo[3,4-d]pyrimidine (5.62 g, 36.36 mmol)** in ethanol (175 mL) at 2O0C under nitrogen. The resulting solution was stirred at 2O0C for 30 minutes and at 5O0C for 10 minutes. The solution was filtered and the filtrate was evaporated. The crude product was purified by flash silica chromatography, elution gradient 2 to 8% MeOH in DCM. Pure fractions were evaporated to dryness to afford methyl 4-(tert- butoxycarbonylamino)- 1 -( 1 H-pyrazo Io [3 ,4-d]pyrimidin-4-yl)piperidine-4-carboxylate (9.94 g, 72.6 %) as a cream dry film, m/z (ESI+) M+ = 377; HPLC tR = 1.24 min; IH NMR (399.9 MHz, DMSO-d6) delta 1.41 (9H, s), 1.92 – 1.97 (2H, m), 2.07 – 2.10 (2H, m), 3.57 (2H, m), 3.63 (3H, s), 4.34 (IH, s), 7.53 (IH, s), 8.24 (IH, s), 8.30 (IH, s), 13.52 (IH, s).H= * Commercially available from Chontech (catalogue number: 07044)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5399-92-8, 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH:ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; ASTRAZENECA AB; WO2008/75109; (2008); A1;,
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.5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H3ClN4, molecular weight is 154.5571, as common compound, the synthetic route is as follows.Quality Control of 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine

To a solution of 4-chloro-lH-pyrazolo[3,4-^pyrimidine (J. Amer. Chem. SQC. 1957, 79, 6407-6413) (51 mg, 0.33 mmol) in ethanol (2 ml) was added triethylamine (100 mul, 0.72 mmol) and 4-(N-Boc-aminomethyl)piperidine (87 mg, 0.41 mmol). The solution was heated at 80 C for 3 hours, and then cooled to room temperature. The solution was evaporated to dryness and the residue purified by recrystallisation (isopropanol) to yield the intermediate NH-BOC protected product (33 mg, 30% yield).To the intermediate NH-BOC protected product (32 mg, 0.096 mmol) was added HCl (1 ml, 4M solution in dioxane, 4 mmol). The suspension was stirred at room temperature for 1 hour, and then diluted with diethyl ether (4 ml). The ethereal layer was discarded and the solid washed with a further portion of diethyl ether (2 ml). The ethereal layer was again discarded, and the resultant solid dried under high vacuum. The free base was liberated by dissolution of this material in methanol, loading onto an acidic resin SCX-2 cartridge, and elution from the cartridge with ammonia in methanol to give the title compound (21 mg, quantitative). LC/MS Rt 0.86 [M+H]+233

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5399-92-8, 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; CANCER RESEARCH TECHNOLOGY LIMITED; WO2006/46023; (2006); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 5399-92-8, 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. 5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H3ClN4, 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 stirred solution of 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (2.5 g, 16.23 mmol, 1 equiv) in DCM (30 mL) was added NBS (3.4 g, 19.48 mmol, 1.2 equiv) at 000. The reaction mixture was warmed to room temperature and stirred for 0/N. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate evaporated to obtain crude which was purified over silica gel flash column chromatography. The compound eluted out in 15% ethyl acetate in n-hexane to afford 3-bromo-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (1.3 g, crude) as pale yellow solid. 1H NMR (400 MHz, DMSO-d6) O ppm – 8.02 (s, 1H), 12.18 (s, 1H), 14.00 (br.s, 1H)

According to the analysis of related databases, 5399-92-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; AXTEN, Jeffrey Michael; FAUCHER, Nicolas Eric; DAUGAN, Alain Claude-Marie; (110 pag.)WO2017/46738; (2017); A1;,
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.5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H3ClN4, molecular weight is 154.5571, as common compound, the synthetic route is as follows.Computed Properties of C5H3ClN4

Example 2 Preparation of 4-(1H-pyrazolo-4-phenoxy)aniline (3a-1) P-aminophenol (0.55g, 5.5mmol) and sodium hydroxide (0.20g, 5.5mmol) were added to 10mL water; potassium carbonate (0.76g, 5.5mmol) was added after resulting mixture was stirred for 30 minutes at normal temperature; the temperature was increased to 60C, and tetrahydrofuran solution of 4-chloro-1H-pyrazolopyrimidine (intermediate 2) (0.94g, 6.6mmol) was slowly added to the reaction solution; after one hour, reaction was stopped; after the tetrahydrofuran of the reaction system was distilled to dryness, the remaining system was extracted with ethyl acetate and water twice; the ethyl acetate layer was dried with anhydrous magnesium sulfate and then spun dry, and then introduced into a column for purification to obtain 0.77g 4-(1H-pyrazolo-4-phenoxy)aniline (3a-1) at a yield of 62.1%. 1H NMR (400 MHz, DMSO-d6): delta 14.07(s, 1H), 8.50(s, 1H), 7.67(s, 1H), 6.96(d, J=8.8 Hz, 2H), 6.64(d, J=8.8 Hz, 2H), 5.20(s, 2H) ppm. LCMS m/z: 228.1 [M + H].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5399-92-8, 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; GUANGXI WUZHOU PHARMACEUTICALS (GROUP) CO., LTD.; YANG, Shengyong; WEI, Yuquan; EP2889298; (2015); 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. 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);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

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. 5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below., HPLC of Formula: C5H3ClN4

Compound 2 (1.88 g, 0.012 mol)was dissolved in EtOAc (50 mL) and heated to 50 C. After 10 min pyridinium 4-toluenesulfonate(PPTs) (50 mg) were added, followed by the addition of 3,4-dihydro-2H-pyran. The resulting reactionmixture was at stirred 50 C. After the reaction was complete according to the TLC detection, themixture was cooled to room temperature, washed with water (60 mL x 1), and a saturated solution ofNaCl (50 mL x 2), and dried over MgSO4. The ethyl acetate was removed and petroleum ether (60 mL x 2) was added. The mixture was heated and filtered through cotton. Removal of petroleum ether invacuo gives compound 3 as light yellow colored solid. Yield: 76.5%. 1H-NMR (400 MHz, DMSO-d6) delta 8.92 (s, 1H), 8.55 (s, 1H), 6.02 (dd, J = 10.4, 2.4 Hz, 1H), 3.97 (d, J = 12.0 Hz, 1H), 3.76-3.70 (m, 1H),2.49-2.42 (m, 1H), 2.07-2.08 (m, 1H), 1.98-1.94 (m, 1H), 1.85-1.73 (m, 1H), 1.64-1.58 (m, 2H). ESI-MSm/z: 239.06 [M + H]+.

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; Fu, Yu; Wang, Yuanyuan; Wan, Shanhe; Li, Zhonghuang; Wang, Guangfa; Zhang, Jiajie; Wu, Xiaoyun; Molecules; vol. 22; 4; (2017);,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 5399-92-8, 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 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.

Preparation of 1H-Pyrazolo[3,4-d]pyrimidine: 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine Pd(OH)2 and are combined in methanol in a reaction vessel. The reaction vessel is evacuated and backfilled with hydrogen gas and the resultant mixture is stirred at rt for several hours. The resultant mixture is filtered and concentrated in vacuo to provide the dehalogenated product, which was used without further purification.

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

Reference:
Patent; ChemoCentryx, Inc.; US2007/10523; (2007); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthetic Route of 5399-92-8, 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. 5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below.

To a suspension of 4-Chloro-lH-pyrazolo [3,4-d] pyrimidine (1. lg, 7.1 mmol) in CHC13 (50 mL) was added NBS (1.49 g, 8. 4 mmol. ) The mixture was stirred at room temperature for 5 hours, cooled to OC and the solids were isolated by vacuum filtration, rinsed with cold CHC13, and air dried. The solid was purified by column chromatography on silica (50% EtOAc/hexanes) to give 3-Bromo-4-chloro-lH-pyrazolo [3, 4-d] pyrimidine (1.3, 77%. )

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,5399-92-8, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; WO2005/51304; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 5399-92-8, 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. 5399-92-8, name is 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine. A new synthetic method of this compound is introduced below.

Slowly add a solution of DIPEA (63g, 0.488mol, Chinese name: N, N-diisopropylethylamine) in THF (50mL) at -20 C to SM (50g, 0.324mol) and 2- (trimethyl In a mixed solution of silyl) ethoxymethyl chloride (62 g, 0.39 mol, SEMCl) in DMF (50 mL) and THF (200 mL), after stirring at -20 C for 3 hours, water was added to quench it, and ethyl acetate Ester extraction, drying the organic phase, filtering, and concentrating to obtain the crude product, which was purified by flash column using petroleum ether and ethyl acetate (v / v = 1/1) as eluent to obtain pale yellow oil A-1 (45g, 0.158 mol, yield: 32.6%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,5399-92-8, 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; Hangzhou Ao Jin Bio-pharmaceutical Co., Ltd.; Yin Jianming; (18 pag.)CN110446713; (2019); A;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia