16019-33-3

Basic information

• Product Name: 5-ACETALDEHYDEYL-4,6-DICHLOROPYRIMIDINE
• Synonyms: 5-ACETALDEHYDEYL-4,6-DICHLOROPYRIMIDINE;(4,6-Dichloro-pyrimidin-5-yl)-acetaldehyde;4,6-Dichloro-5-pyrimidineacetaldehyde;2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde;4,6-Dichloropyrimidine-5-acetaldehyde;5-PyriMidineacetaldehyde, 4,6-dichloro-;4,6-Dichloro-pyriMidine-5-yl-acetaldehyde;(4,6-dichloro-5-pyriMidinyl)acetaldehyde
• CAS NO: 16019-33-3
• Molecular Formula: C₆H₄Cl₂N₂O
• Molecular Weight: 191.017
• Mol File: 16019-33-3.mol
• Article Data: 20

Chemical Properties

• Melting Point: 89-91 °C(Solv: dichloromethane (75-09-2); heptane (142-82-5))
• Boiling Point: 312.714 °C at 760 mmHg
• Flash Point: 142.924 °C
• Appearance: /
• Density: 1.47 g/cm³
• Refractive Index: 1.559
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: -4.49±0.26(Predicted)
• CAS DataBase Reference: 5-ACETALDEHYDEYL-4,6-DICHLOROPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-ACETALDEHYDEYL-4,6-DICHLOROPYRIMIDINE(16019-33-3)
• EPA Substance Registry System: 5-ACETALDEHYDEYL-4,6-DICHLOROPYRIMIDINE(16019-33-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 16019-33-3(Hazardous Substances Data)

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

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

Downstream Products

• 1001398-62-4 1-methylethyl 4-{[7-(4-bromo-3-fluorophenyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy}-1-piperidinecarboxylate 
• 1001398-63-5 1-methylethyl 4-{[7-(4-cyano-3-fluorophenyl)-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy}-1-piperidinecarboxylate 
• 1416273-10-3 C₂₂H₂₇FN₄O₅S 
• 1001399-10-5 1-methylethyl 4-[(7-{4-[(dimethylamino)sulfonyl]phenyl}-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]-1-piperidinecarboxylate 
• 1001399-38-7 1-methylethyl 4-({7-[2-fluoro-4-(methylthio)phenyl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl}oxy)-1-piperidinecarboxylate 
• 1416273-12-5 C₂₃H₃₀N₄O₅S 
• 1416273-11-4 C₁₄H₁₄ClN₃S 
• 1001399-09-2 4-(4-chloro-5,6-dihydro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-N,N-dimethylbenzenesulfonamide 
• 1416272-94-0 C₂₃H₃₀N₄O₃S 
• 212268-44-5 4-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine 

Relevant articles and documents

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.

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.

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.