52026-43-4

Basic information

• Product Name: 4-(2-CHLORO-6-METHYLPYRIMIDIN-4-YL)MORPHOLINE
• Synonyms: 4-(2-CHLORO-6-METHYLPYRIMIDIN-4-YL)MORPHOLINE;4-(2-chloro-6-methyl-4-pyrimidinyl)Morpholine
• CAS NO: 52026-43-4
• Molecular Formula: C₉H₁₂ClN₃O
• Molecular Weight: 213.66408
• Mol File: 52026-43-4.mol

Chemical Properties

• Boiling Point: 397.6°C at 760 mmHg
• Flash Point: 194.3°C
• Appearance: /
• Density: 1.276g/cm³
• Vapor Pressure: 1.56E-06mmHg at 25°C
• Refractive Index: 1.557
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 5.06±0.41(Predicted)
• CAS DataBase Reference: 4-(2-CHLORO-6-METHYLPYRIMIDIN-4-YL)MORPHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-CHLORO-6-METHYLPYRIMIDIN-4-YL)MORPHOLINE(52026-43-4)
• EPA Substance Registry System: 4-(2-CHLORO-6-METHYLPYRIMIDIN-4-YL)MORPHOLINE(52026-43-4)

Safety Data

• Hazardous Substances Data: 52026-43-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(2-CHLORO-6-METHYLPYRIMIDIN-4-YL)MORPHOLINE is used as a key intermediate in the synthesis of various drugs for the treatment of diseases. Its unique structure allows it to be a building block in the development of new pharmaceutical compounds, contributing to the advancement of medicine.
Used in Agrochemical Industry:
4-(2-CHLORO-6-METHYLPYRIMIDIN-4-YL)MORPHOLINE is used as a precursor in the production of pesticides for crop protection. Its chemical properties make it suitable for creating effective and targeted agrochemicals, ensuring the health and productivity of agricultural crops.
Used in Organic Chemistry:
4-(2-CHLORO-6-METHYLPYRIMIDIN-4-YL)MORPHOLINE is utilized as a versatile building block in organic chemistry, enabling the creation of a wide range of chemical compounds. Its presence in various synthesis processes highlights its importance in the development of new chemical entities for various applications.

InChI:InChI=1/C9H12ClN3O/c1-7-6-8(12-9(10)11-7)13-2-4-14-5-3-13/h6H,2-5H2,1H3

Upstream product

• 626-48-2 6-Methyluracil 
• 110-91-8 morpholine 
• 5424-21-5 2,4-dichloro-6-methylpyrimidine 

Downstream Products

• 169882-37-5 N-(2-bromo-4-(1-methylethyl)phenyl)-N-ethyl-4-morpholino-6-methyl-2-pyrimidinamine 
• 1416913-56-8 C₃₅H₄₄N₈O₄ 
• 77965-40-3 (4-Methyl-6-morpholin-4-yl-pyrimidin-2-ylsulfanyl)-acetic acid hydrazide 

Relevant articles and documents

Exploring the potential of newly synthesized 4-methyl-6-morpholino-pyrimidine derivatives as antiproliferative agents

In view of exploring the potential of pyrimidine derivatives as anticancer agents, a series of 4-methyl-6-morpholinopyrimidine derivatives was synthesised and characterised by NMR (1H & 13C), SC-XRD and mass spectral analysis. The in vitro anticancer activity of these compounds was investigated using different human cancer cell lines, namely HeLa (cervix), NCI-H460 (lung), MCF-7 (breast), HepG2 (liver) and IMR-32 (brain). Compounds 4c and 5h exhibited potent anticancer activity in a dose-dependent manner as compared to other derivatives, with IC50 values of 5.88 ± 1.22 and 6.11 ± 2.12 μM on HeLa and NCI-H460, cells respectively. The inhibitory effect of 4c and 5h on cancer cell proliferation was shown to be a consequence of reactive oxygen species (ROS) generation and subsequent induction of cellular apoptosis, as evidenced by an increase in hypodiploid (subG1) population, early apoptotic cell population, caspase-3/7 activity, loss of mitochondrial membrane potential and degradation of nuclear DNA. Furthermore, molecular docking studies revealed that 4c and 5h compounds bind to the ATP binding pocket of the mammalian target of rapamycin (mTOR). Based on our results, we conclude that 4-methyl-6-morpholinopyrimidine derivatives prevent cancer cell proliferation by inducing apoptosis and thus have potential to be further explored for anticancer properties.

A natural product inspired hybrid approach towards the synthesis of novel pentamidine based scaffolds as potential anti-parasitic agents

A natural product inspired molecular hybridization approach led us to a series of novel pentamidine based pyrimidine and chalcone scaffolds. All the hybrids were evaluated for their anti-leishmanial potential. Most of the screened compounds have showed significant in vitro anti-leishmanial activity with less cytotoxicity in comparison to the standard drugs (pentamidine, sodium stibogluconate, and miltefosine). Additionally, anti-malarial screening of these compounds was also done and four compounds have shown superior activity against chloroquine resistance strain (K1) of Plasmodium falciparum.

MODULATORS FOR AMYLOID BETA

The invention relates to compounds of formula wherein the substituents are as described in claim 1. Compounds of formula I are modulators for amyloid beta and thus, they may be useful for the treatment or prevention of a disease associated with the deposi

1N-ALKYL-N-ARYLPYRIMIDINAMINES AND DERIVATIVES THEREOF

The present invention provides novel compounds, compounds and pharmaceutical compositions thereof, and methods of using same in the treatment of affective disorders, anxiety, depression, post-traumatic stress disorders, eating disorders, supranuclear palsy, irritable bowel syndrome, immune suppression, Alzheimer'disease, gastrointestinal diseases, anorexia nervosa, drug and alcohol withdrawal symptoms, drug addiction, inflammatory disorders, or fertility problems. The novel compounds provided by this invention are those of formula: wherein R 1, R 3, R 4, R 5, Z, Y, V, X, X', J, K, L, and M are as defined herein.

1N-alkyl-N-arylpyrimidinamines and derivatives thereof

The present invention provides novel compounds, compounds and pharmaceutical compositions thereof, and methods of using same in the treatment of affective disorders, anxiety, depression, post-traumatic stress disorders, eating disorders, supranuclear palsy, irritable bowel syndrome, immune suppression, Alzheimer's disease, gastrointestinal diseases, anorexia nervosa, drug and alcohol withdrawal symptoms, drug addiction, inflammatory disorders, or fertility problems. The novel compounds provided by this invention are those of formula: wherein R1, R3, R4, R5, Z, Y, V, X, X', J, K, L, and M are as defined herein.

Non-peptide corticotropin-releasing hormone antagonists: Syntheses and structure activity relationships of 2-anilinopyrimidines and -triazines

Screening of our chemical library using a rat corticotropin-releasing hormone (CRH) receptor assay led to the discovery that 2-anilinopyrimidine 15-1 weakly displaced [125I]-0-Tyr-oCRH from rat frontal cortex homogenates when compared to the known peptide antagonist α-helical CRH(9- 41) (K(i) = 5700 nM vs 1 nM). Furthermore, 15-1 weakly inhibited CRH- stimulated adenylate cyclase activity in the same tissue, but it was less potent than α-helical CRH(9-41) (IC50 = 20 000 nM vs 250 nM). Systematic structure-activity relationship studies, using the cloned human CRH1 receptor assay, defined the pharmacophore for optimal binding to hCRH1 receptors. Several high-affinity 2-anilinopyrimidines and -triazines were discovered, some of which had superior pharmacokinetic profiles in the rat. This paper describes the structure-activity studies which improved hCRH1 receptor binding affinity and pharmacokinetic parameters in the rat. Compound 28-17 (mean hCRH(1)K(1) = 32 nM) had a significantly improved pharmacokinetic profile in the rat (19% oral bioavailability at 30 mg/kg) as well as in the dog (20% oral bioavailability at 5 mg/kg) relative to the early lead structures.