- Process for synthesizing 2-(4,6-dichloropyrimidine-5-yl) acetaldehyde through continuous flow ozonation
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The invention discloses a process for synthesizing 2-(4,6-dichloropyrimidine-5-yl) acetaldehyde by continuous flow ozonation, which comprises the following steps: by using 5-allyl-4,6-dichloropyrimidine as a raw material, carrying out continuous flow ozonation, and carrying out sodium thiosulfate reduction to obtain the target product. The invention provides a brand-new continuous flow process forozonization synthesis of 2-(4,6-dichloropyrimidine-5-yl) acetaldehyde, which is safe, simple to operate, efficient and easy for large-scale production.
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Paragraph 0032-0034; 0046-0047
(2020/08/06)
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- New compound, preparation method and application thereof
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Belonging to the technical field of organic chemistry, the invention provides a new compound, a preparation method and application thereof. The compound is named 4, 6-dichloropyrimidine-5-acetaldehyde-O-methyl oxime, has a molecular formula of C7H7Cl2N3O and a relative molecular mass of 220.06, and is a light yellow solid in appearance. The preparation method of the new compound has the advantagesof easily available raw materials, simple operation, good product purity, high yield, etc., and is easy for industrial production. The new compound 4, 6-dichloropyrimidine-5-acetaldehyde-O-methyl oxime can be subjected to one-step reaction to obtain 4, 6-dichloropyrimidine-5-acetaldehyde. The new compound can be applied as an important intermediate in pharmaceutical field.
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Paragraph 0071; 0072; 0073
(2019/05/16)
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- Method for preparing 4, 6-dichloropyrimidine-5-acetaldehyde
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The invention discloses a method for preparing 4, 6-dichloropyrimidine-5-acetaldehyde, and belongs to the field of organic chemistry. According to the technical scheme, diethyl malonate is added intoan organic solvent, alkali and 2-bromomethyl-1, 3-dioxolane are added, the mixture is heated to 60-70 DEG C, reacting is carried out for 2-4 hours, after water is added, extracting is carried out by using methyl tert-butyl ether, and the methyl tert-butyl ether is evaporated to obtain a first intermediate; sodium alkoxide is added into an organic alcohol solution, formamidine acetate is added, stirring is carried out at room temperature for 30-45min, the first intermediate is added for reacting for 20-30h, the filtrate is evaporated, recrystallizing is carried out by using ethanol to obtain asecond intermediate; the second intermediate is added into a chlorination reagent, heating and refluxing are carried out for 10-15h, ice water is poured in, extracting is carried out by using ethyl acetate, the ethyl acetate is evaporated to obtain a third intermediate which is added into acidic solution for heating for 2-4h, and then cooled down to room temperature, extracting is carried out by using dichloromethane, drying is carried out by using anhydrous sodium sulfate, then the dichloromethane is evaporated to dryness, and petroleum ether is recrystallized to obtain the 4, 6-dichloropyrimidine-5-acetaldehyde. According to the invention, the risk of explosion is reduced, the requirement of experimental equipment is low, and the requirement of batch production is met.
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Paragraph 0038; 0041-0043
(2019/04/26)
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- 4-chloro-7H-pyrrolo[2,3-d]pyrimidine synthetic method
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The invention discloses a 4-chloro-7H-pyrrolo[2,3-d]pyrimidine synthetic method. A compound is an important intermediate for synthesizing ruxolitinib and tofacitinib as a JAK inhibitor for treating rheumatoid arthritis. The 4-chloro-7H-pyrrolo[2,3-d]pyrimidine synthetic method comprises the following steps of by taking a compound I (4,6-dichloro-5-allyl pyrimidine) as a starting material, performing oxidation reaction on the compound I and ozone to produce a compound II; then performing nucleophilic substitution reaction on the compound II and triethyl orthoformate to produce a compound III; then performing nucleophilic substitution reaction on the compound III and ammonia gas to produce a compound IV; and finally, performing ring closing on the compound IV self in an acid environment to produce a compound V, i.e., 4-chloro-7H-pyrrolo[2,3-d]pyrimidine, wherein a synthetic route is shown as the following formula (described in the description). The synthetic method disclosed by the invention is cheap and available in raw materials, simple and short in synthetic route, low in cost, high in yield and easy in industrial production.
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Paragraph 0038; 0040; 0043; 0046; 0048; 0049; 0052
(2018/09/11)
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- An improved synthesis of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine
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[Figure not available: see fulltext.] An improved seven-step synthesis of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine from dimethyl malonate with 31% overall yield is described. The procedure is operationally simple and practical for the synthesis of the 4-chloro-7H-pyrrolo[2,3-d]pyrimidine building block.
- Zhang, Yu-Liu,Xu, Cheng-Tao,Liu, Ting,Zhu, Yong,Luo, Yu
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p. 638 - 642
(2018/08/17)
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- ATROPISOMERISM FOR ENHANCED KINASE INHIBITOR SELECTIVITY
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The invention provides a series of conformationally stable and selective kinase inhibitors, and methods of using the kinase inhibitors. The effect of atropisomerism on kinase selectivity was assessed, finding improved selectivity compared to rapidly inter
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Page/Page column 33
(2019/01/10)
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- METHODS FOR PREPARATION OF (4,6-DIHALO-PYRIMIDIN-5-YL)-ACETALDEHYDES
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This invention relates to the synthesis of chemical compounds and particularly to methods for the preparation of (4,6-dihalo-pyrimidin-5-yl)-acetaldehydes. The methods involve preparing a compound of the following general formula V from a compound of the following general formula IV through hydrolysis under the action of mercury dichloride and calcium carbonate, according to the following equation: wherein X is Cl or Br. The methods offer the benefits of use of highly available materials, high step yields, moderate reaction conditions, simply post-processing and purification, and suitability to industrialized production.
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Paragraph 0034; 0035
(2016/03/12)
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- Exploiting Atropisomerism to Increase the Target Selectivity of Kinase Inhibitors
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Many biologically active molecules exist as rapidly interconverting atropisomeric mixtures. Whereas one atropisomer inhibits the desired target, the other can lead to off-target effects. Herein, we study atropisomerism as a possibility to improve the sele
- Smith, Davis E.,Marquez, Isaac,Lokensgard, Melissa E.,Rheingold, Arnold L.,Hecht, David A.,Gustafson, Jeffrey L.
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supporting information
p. 11754 - 11759
(2015/10/05)
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- INDOLE-SUBSTITUTED PYRROLOPYRIMIDINYL INHIBITORS OF Uba6
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Disclosed are chemical entities that inhibit Uba6, each of which is a compound of Formula /: Formula (I) or a pharmaceutically acceptable salt thereof, wherein R*1 is -H or -CH3; and Y is Formula (II) or Formula (III), wherein R
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Paragraph 0108
(2014/02/16)
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- CYCLOLIC HYDRAZINE DERIVATIVES AS HIV ATTACHMENT INHIBITORS
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Compounds of Formula I are provided, including pharmaceutically acceptable salts thereof: wherein A is selected from the group consisting of: wherein Z is selected from the group consisting of: which are useful as HIV attachment inhibitors.
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Page/Page column 61-62
(2013/09/26)
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- Discovery of 6,7-dihydro-5H-pyrrolo[2,3-a]pyrimidines as orally available g protein-coupled receptor 119 agonists
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GPR119 is a 7-transmembrane receptor that is expressed in the enteroendocrine cells in the intestine and in the islets of Langerhans in the pancreas. Indolines and 6,7-dihydro-5H-pyrrolo[2,3-a]pyrimidines were discovered as G protein-coupled receptor 119
- Katamreddy, Subba R.,Carpenter, Andrew J.,Ammala, Carina E.,Boros, Eric E.,Brashear, Ron L.,Briscoe, Celia P.,Bullard, Sarah R.,Caldwell, Richard D.,Conlee, Christopher R.,Croom, Dallas K.,Hart, Shane M.,Heyer, Dennis O.,Johnson, Paul R.,Kashatus, Jennifer A.,Minick, Doug J.,Peckham, Gregory E.,Ross, Sean A.,Roller, Shane G.,Samano, Vicente A.,Sauls, Howard R.,Tadepalli, Sarva M.,Thompson, James B.,Xu, Yun,Way, James M.
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p. 10972 - 10994
(2013/02/25)
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- FUSED BICYCLIC PYRIMIDINE DERIVATIVES AND METHODS OF USE THEREOF
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The present invention relates to Fused Bicyclic Pyrimidine Derivatives, compositions comprising a Fused Bicyclic Pyrimidine Derivative, and methods of using the Fused Bicyclic Pyrimidine Derivatives for treating or preventing obesity, diabetes, a metabolic disorder, a cardiovascular disease or a disorder related to the activity of a G-protein coupled receptor (GPCR) in a patient.
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Page/Page column 34
(2011/06/19)
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- BICYCLIC HETEROCYCLE DERIVATIVES AND USE THEREOF AS GPR119 MODULATORS
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The present invention relates to Bicyclic Heterocycle Derivatives of Formula (I), compositions comprising a Bicyclic Heterocycle Derivative, and methods of using the Bicyclic Heterocycle Derivatives for treating or preventing obesity, diabetes, a metaboli
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Page/Page column 76-77
(2010/04/03)
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- BICYCLIC HETEROCYCLE DERIVATIVES AND THEIR USE AS GPCR MODULATORS
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The present invention relates to Bicyclic Heterocycle Derivatives of Formula (I), compositions comprising a Bicyclic Heterocycle Derivative, and methods of using the Bicyclic Heterocycle Derivatives for treating or preventing obesity, diabetes, a diabetic
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Page/Page column 45
(2010/04/03)
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- BICYCLIC HETEROCYCLE DERIVATIVES AND METHODS OF USE THEREOF
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The present invention relates to Bicyclic Heterocycle Derivatives, compositions comprising a Bicyclic Heterocycle Derivative, and methods of using the Bicyclic Heterocycle Derivatives for treating or preventing obesity, diabetes, a diabetic complication,
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Page/Page column 73-74
(2010/04/03)
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- Facile reductive amination of aldehydes with electron-deficient anilines by acyloxyborohydrides in TFA: Application to a diazaindoline scale-up
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A scale-up of diazaindoline 1 was achieved in four stages and 32% overall yield. The key step involved rapid reductive animation of aldehyde 8 with aniline 5 by sodium triacetoxyborohydride (STAB-H) and TFA followed by ring closure of intermediate amine 9
- Boros, Eric E.,Thompson, James B.,Katamreddy, Subba R.,Carpenter, Andrew J.
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experimental part
p. 3587 - 3590
(2009/09/05)
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- GPR119 AGONISTS FOR THE TREATMENT OF DIABETES AND RELATED DISORDERS
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The present invention relates to novel compounds that are useful in the treatment of metabolic disorders, particularly Type II diabetes mellitus and related disorders, and also to the methods for the making and use of such compounds.
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Page/Page column 171
(2010/11/29)
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- Phosphoramidate protides of carbocyclic 2′,3′-dideoxy-2′, 3′-didehydro-7-deazaadenosine with potent activity against HIV and HBV
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Synthesis of phosphoramidate protides of carbocyclic D- and L-2′,3′-dideoxy-2′,3′-didehydro-7-deazaadenosine by treatment of the nucleoside with phosphorochloridates in the presence of pyridine and t-BuMgCl is described. Several of these protides showed s
- Gudmundsson, Kristjan S.,Wang, Zhicheng,Daluge, Susan M.,Johnson, Lance C.,Hazen, Richard,Condreay, Lynn D.,McGuigan, Christopher
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p. 1929 - 1937
(2007/10/03)
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- CARBOCYCLIC NUCLEOSIDE DERIVATIVES AS INHIBITORS OF RNA-DEPENDENT RNA VIRAL POLYMERASE
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The present invention provides carbocyclic nucleoside compounds and certain derivatives thereof which are inhibitors of RNA-dependent RNA viral polymerase. These compounds are inhibitors of RNA-dependent RNA viral replication and are useful for the treatment of RNA-dependent RNA viral infection. They are particularly useful as inhibitors of hepatitis C virus (HCV) NS5B polymerase, as inhibitors of HCV replication, and/or for the treatment of hepatitis C infection. The invention also describes pharmaceutical compositions containing such carbocyclic nucleoside compounds alone or in combination with other agents active against RNA-dependent RNA viral infection, in particular HCV infection. Also disclosed are methods of inhibiting RNA-dependent RNA polymerase, inhibiting RNA-dependent RNA viral replication, and/or treating RNA-dependent RNA viral infection with the carbocyclic nucleoside compounds of the present invention
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- Synthesis of some pyrrolo[2,3-d]pyrimidine and 1,2,3-triazole isonucleosides
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Nucleoside analogues 8, 9, 10 and 11, in which a pyrrolo[2,3-d]pyrimidine ring is linked to a 2-hydroxymethyl-3-hydtoxytetrahydrofuran have been prepared The azide 16 used as an intermediate in the mutes to these compounds also gave access to the 1,2,3-triazole isonucleosides 12 and 13.
- Talekar, Ratnakar R.,Wightman, Richard H.
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p. 3831 - 3842
(2007/10/03)
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