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Cas Database

22536-61-4

22536-61-4

Identification

Synonyms:AC-248;2-chloro-5-methyl pyrimidine;5-methyl-2-chloropyrimidine;2-Chlor-5-methylpyrimidin;

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Safety information and MSDS

  • Pictogram(s):Xn

  • Hazard Codes:Xn

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  • Manufacture/Brand:TRC
  • Product Description:2-Chloro-5-methylpyrimidine
  • Packaging:500mg
  • Price:$ 75
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:2-Chloro-5-methylpyrimidine
  • Packaging:100mg
  • Price:$ 60
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Chloro-5-methylpyrimidine >98.0%(GC)
  • Packaging:5g
  • Price:$ 118
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Chloro-5-methylpyrimidine >98.0%(GC)
  • Packaging:1g
  • Price:$ 36
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Chloro-5-methylpyrimidine 98%
  • Packaging:5 g
  • Price:$ 24
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Chloro-5-methylpyrimidine 98%
  • Packaging:25 g
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:2-Chloro-5-methylpyrimidine 97%
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  • Manufacture/Brand:Matrix Scientific
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Relevant articles and documentsAll total 13 Articles be found

Synthesis method 2 -fluoro -5 -trifluoromethyl pyrimidine

-

, (2021/10/20)

The invention relates to the technical field of drug synthesis, and provides a synthesis method of 2 -fluoro -5 -trifluoromethyl pyrimidine. 5 - Methyluracil is used as a raw material and is subjected to cyclic chlorination reaction. Redox reaction, chlorination reaction and fluorination reaction obtain the target product, the process is simple, the raw materials are cheap and easily available, the yield is high, and no heavy metal pollution is generated in the whole process. In the chlorination reaction, phosphorus oxychloride is used for chlorination, chlorine is used for chlorination in the chlorination reaction, the cost of the chlorination reaction is low, phosphorus pentachloride is used for recycling phosphorus oxychloride in the cyclochlorination reaction, and the reaction cost can be further reduced.

Discovery of (10 R)-7-Amino-12-fluoro-2,10,16-trimethyl-15-oxo-10,15,16,17- tetrahydro- 2H -8,4-(metheno)pyrazolo[4,3- h ][2,5,11]- benzoxadiazacyclotetradecine-3-carbonitrile (PF-06463922), a macrocyclic inhibitor of anaplastic lymphoma kinase (ALK) and c-ros oncogene 1 (ROS1) with preclinical brain exposure and broad-spectrum potency against ALK-resistant mutations

Johnson, Ted W.,Richardson, Paul F.,Bailey, Simon,Brooun, Alexei,Burke, Benjamin J.,Collins, Michael R.,Cui, J. Jean,Deal, Judith G.,Deng, Ya-Li,Dinh, Dac,Engstrom, Lars D.,He, Mingying,Hoffman, Jacqui,Hoffman, Robert L.,Huang, Qinhua,Kania, Robert S.,Kath, John C.,Lam, Hieu,Lam, Justine L.,Le, Phuong T.,Lingardo, Laura,Liu, Wei,McTigue, Michele,Palmer, Cynthia L.,Sach, Neal W.,Smeal, Tod,Smith, Graham L.,Stewart, Albert E.,Timofeevski, Sergei,Zhu, Huichun,Zhu, Jinjiang,Zou, Helen Y.,Edwards, Martin P.

supporting information, p. 4720 - 4744 (2014/07/07)

Although crizotinib demonstrates robust efficacy in anaplastic lymphoma kinase (ALK)-positive non-small-cell lung carcinoma patients, progression during treatment eventually develops. Resistant patient samples revealed a variety of point mutations in the kinase domain of ALK, including the L1196M gatekeeper mutation. In addition, some patients progress due to cancer metastasis in the brain. Using structure-based drug design, lipophilic efficiency, and physical-property-based optimization, highly potent macrocyclic ALK inhibitors were prepared with good absorption, distribution, metabolism, and excretion (ADME), low propensity for p-glycoprotein 1-mediated efflux, and good passive permeability. These structurally unusual macrocyclic inhibitors were potent against wild-type ALK and clinically reported ALK kinase domain mutations. Significant synthetic challenges were overcome, utilizing novel transformations to enable the use of these macrocycles in drug discovery paradigms. This work led to the discovery of 8k (PF-06463922), combining broad-spectrum potency, central nervous system ADME, and a high degree of kinase selectivity.

CYCLOHEXANE ANALOGUES AS GPR119 AGONISTS

-

Page/Page column 8, (2012/03/12)

This invention relates to a series of substituted cyclohexane containing analogues which are agonists of GPR119 intended to treat metabolic diseases mediated by GPR119 including Type I & II diabetes mellitus. Diabetes mellitus is an ever-increasing threat to human health causing various complications (blindness, kidney failure, neuropathy, heart attack, stroke, etc.). Recently it was found that activation of GPR119 which is highly expressed in pancreatic beta cells causes glucose dependent insulin secretion and GLP-1 release. Many pharmaceuticals are currently developing GPR119 agonists and herein we disclose alternative GPR119 agonists. Our invention describes GPR119 agonists having structural Formula (I), pharmaceutically acceptable salt or solvate of Formula (I), isomer or prodrug of Formula (I), and combination therapy of Formula (I) with other anti-diabetic drugs like DPP-IV inhibitors and/or insulin sensitizers.

Process route upstream and downstream products

Process route

5-methyl-2,4,6-trichloropyrimidine
1780-36-5

5-methyl-2,4,6-trichloropyrimidine

5-methylpyrimidine
2036-41-1

5-methylpyrimidine

2-chloro-5-methylpyrimidine
22536-61-4

2-chloro-5-methylpyrimidine

Conditions
Conditions Yield
With water; zinc;
5-methyl-2,4,6-trichloropyrimidine
1780-36-5

5-methyl-2,4,6-trichloropyrimidine

water
7732-18-5

water

5-methylpyrimidine
2036-41-1

5-methylpyrimidine

2-chloro-5-methylpyrimidine
22536-61-4

2-chloro-5-methylpyrimidine

Conditions
Conditions Yield
2,6-dichloro-5-methylpyrimidine
1780-31-0

2,6-dichloro-5-methylpyrimidine

2-chloro-5-methylpyrimidine
22536-61-4

2-chloro-5-methylpyrimidine

Conditions
Conditions Yield
With zinc; In water; at 95 - 105 ℃; for 5h;
81.4%
With zinc; In water; for 3h; Reflux;
78%
With zinc; In water; for 3h; Reflux;
78%
With ammonium hydroxide; zinc; In water; benzene; for 18h; Reflux;
77%
With water; zinc; Reflux;
75%
2,6-dichloro-5-methylpyrimidine; With acetic acid; zinc; In tetrahydrofuran; for 3.66667h;
With sodium hydroxide; water; In dichloromethane; ethyl acetate;
69%
2,6-dichloro-5-methylpyrimidine; With zinc; In tetrahydrofuran; Heating / reflux;
With acetic acid; In tetrahydrofuran; for 2h; Heating / reflux;
60%
With ammonia; water; zinc; In benzene; Heating / reflux;
With ammonia; zinc; In water; benzene; Heating / reflux;
5-methyl-pyrimidin-2-(1H)-one
41398-85-0

5-methyl-pyrimidin-2-(1H)-one

2-chloro-5-methylpyrimidine
22536-61-4

2-chloro-5-methylpyrimidine

Conditions
Conditions Yield
With trichlorophosphate; at 90 ℃;
2.8 g
trimethylaluminum
75-24-1

trimethylaluminum

5-Bromo-2-chloropyrimidine
32779-36-5

5-Bromo-2-chloropyrimidine

2-chloro-5-methylpyrimidine
22536-61-4

2-chloro-5-methylpyrimidine

Conditions
Conditions Yield
With tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; for 24h; Heating;
81%
2-chloro-5-methylpyrimidine
22536-61-4

2-chloro-5-methylpyrimidine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: trichlorophosphate; triethylamine hydrochloride / 5 h / 100 - 110 °C
1.2: 2 h / 40 °C
2.1: zinc / water / 5 h / 95 - 105 °C
With triethylamine hydrochloride; zinc; trichlorophosphate; In water;
2-chloro-5-methylpyrimidine
22536-61-4

2-chloro-5-methylpyrimidine

Conditions
Conditions Yield
5-Methylpyrimidin-2-on, POCl3, Δ, 2523;
4-Methylpyrazol, CHCl3;
2-chloro-5-methylpyrimidine
22536-61-4

2-chloro-5-methylpyrimidine

2-chloro-5-(trifluoromethyl)pyrimidine
69034-12-4

2-chloro-5-(trifluoromethyl)pyrimidine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 1.) HCl, 2.) N-chlorosuccinimide / 2.) CCl4, irradiation, reflux, 4 h
2: 51 percent / SbF5 / 1.) 50 deg C, 35 min, 2.) 150 deg C, 15 min
With hydrogenchloride; N-chloro-succinimide; antimony pentafluoride;
potassium (E)-trifluoro(prop-1-en-1-yl)trifluoroborate

potassium (E)-trifluoro(prop-1-en-1-yl)trifluoroborate

2-chloro-5-methylpyrimidine
22536-61-4

2-chloro-5-methylpyrimidine

(E)-5-methyl-2-(prop-1-en-1-yl)pyrimidine

(E)-5-methyl-2-(prop-1-en-1-yl)pyrimidine

Conditions
Conditions Yield
With potassium phosphate; In 1,4-dioxane; water; at 90 ℃; for 16.5h; Inert atmosphere;
100%
With potassium phosphate; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); In 1,4-dioxane; water; at 90 ℃; for 16.5h; Inert atmosphere;
100%
With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); potassium acetate; In 1,4-dioxane; water; at 90 ℃; for 16.5h; Inert atmosphere;
100%
With potassium phosphate; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); In 1,4-dioxane; water; at 90 ℃; for 16.5h; Reagent/catalyst; Temperature; Inert atmosphere;
100%
With potassium phosphate; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); In 1,4-dioxane; water; at 90 ℃; for 16.5h; Inert atmosphere;
100%
With (4-(N,N-dimethylamino)phenyl)-di-tert-butylphosphine; In 1,4-dioxane; water; at 90 ℃; for 16.5h; Inert atmosphere;
100%
With potassium phosphate; In 1,4-dioxane; water; at 90 ℃; for 16.5h; Inert atmosphere;
100%
With potassium phosphate; 1,1-bis[di-t-butyl-p-methylaminophenyl]palladium(II) chloride; In 1,4-dioxane; at 90 ℃; for 16.5h; Inert atmosphere;
100%
With potassium phosphate; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); In 1,4-dioxane; water; at 90 ℃; for 16.5h; Inert atmosphere;
100%
2-chloro-5-methylpyrimidine
22536-61-4

2-chloro-5-methylpyrimidine

5-methylpyrimidin-2-amine
50840-23-8

5-methylpyrimidin-2-amine

Conditions
Conditions Yield
With ammonia; In ethanol; water; at 200 ℃; for 4h; Time; Sealed tube;
92%
With ammonia; In water; at 200 ℃; for 4h; Sealed tube;
92%
With ethanol; ammonia; at 200 ℃; im Rohr;
With ammonium hydroxide; at 85 ℃; for 18h; Sealed tube;

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