16019-33-3

Usage

Chemical Properties

Crystalline solid

InChI:InChI=1/C6H4Cl2N2O/c7-5-4(1-2-11)6(8)10-3-9-5/h2-3H,1H2

Upstream product

• 16019-30-0 5-allyl-6-hydroxy-3H-pyrimidin-4-one 
• 16019-30-0 6-hydroxy-5-(2-propen-1-yl)-4(1H)-pyrimidinone 
• 886599-20-8 4,6-dichloro-5-[1,3]dioxolan-2-ylmethyl-pyrimidine 
• 2049-80-1 (2-propenyl)propanedioic acid diethyl ester 
• 16019-30-0 5-(prop-2-en-1-yl)pyrimidine-4,6-diol 
• 16019-31-1 5-allyl-4,6-dichloropyrimidine 

Downstream Products

• 14052-82-5 4,6-dichloro-5-(2,2-diethoxyethyl)pyrimidine 
• 1001398-61-3 7-(4-bromo-3-fluorophenyl)-4-chloro-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine 
• 875251-47-1 2-(pyrimidin-5-yl)ethan-1-ol 
• 212268-44-5 4-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine 

Relevant academic research and scientific papers

Process for synthesizing 2-(4,6-dichloropyrimidine-5-yl) acetaldehyde through continuous flow ozonation

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.

New compound, preparation method and application thereof

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.

Method for preparing 4, 6-dichloropyrimidine-5-acetaldehyde

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.

ATROPISOMERISM FOR ENHANCED KINASE INHIBITOR SELECTIVITY

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

An improved synthesis of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine

[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.

4-chloro-7H-pyrrolo[2,3-d]pyrimidine synthetic method

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.

METHODS FOR PREPARATION OF (4,6-DIHALO-PYRIMIDIN-5-YL)-ACETALDEHYDES

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.

Exploiting Atropisomerism to Increase the Target Selectivity of Kinase Inhibitors

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

INDOLE-SUBSTITUTED PYRROLOPYRIMIDINYL INHIBITORS OF Uba6

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

CYCLOLIC HYDRAZINE DERIVATIVES AS HIV ATTACHMENT INHIBITORS

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.