5018-41-7

Usage

Uses

4-Amino-6-chloro-5-methoxypyrimidine is used in the pharmaceutical industry as an intermediate compound for the synthesis of various drugs. Its unique chemical structure allows it to be a key component in the development of new medications, particularly those targeting specific biological pathways or receptors.
Used in Chemical Research:
4-Amino-6-chloro-5-methoxypyrimidine serves as a valuable research tool in the field of organic chemistry. It is used to study the properties and reactions of pyrimidine derivatives, which can lead to the discovery of new chemical compounds and applications.
Used in Material Science:
In the field of material science, 4-Amino-6-chloro-5-methoxypyrimidine is utilized in the development of new materials with specific properties. Its chemical structure can be incorporated into the design of advanced materials, such as sensors, catalysts, or functional polymers, to achieve desired characteristics.

InChI:InChI=1/C5H6ClN3O/c1-10-3-4(6)8-2-9-5(3)7/h2H,1H3,(H2,7,8,9)

Upstream product

• 5018-38-2 4,6-dichloro-5-methoxypyrimidine 

Downstream Products

• 38953-42-3 4-chloro-5-hydroxy-6-aminopyrimidine 
• 695-86-3 amino-4 methoxy-5 pyrimidine 
• 1428248-77-4 6-(4-{4-[4-fluoro-3-(trifluoromethyl)phenyl]-1-methyl-1H-imidazol-2-yl}piperidin-1-yl)-5-methoxy pyrimidin-4-amine 
• 5018-45-1 5,6-dimethoxypyrimidin-4-amine 

Relevant academic research and scientific papers

Development of a Scalable Synthesis of 4-Aminopyrimidin-5-ol, a Versatile Intermediate

A robust process for the preparation of multigram quantities of 4-aminopyrimidin-5-ol (5) in good yield from an inexpensive and readily available pyrimidine starting material is described. An initial evaluation of the reported literature route for this material utilizing a de novo pyrimidine synthesis provided safety concerns over the scalability of several intermediates. In addition, a number of steps proceeded in mediocre yield, and involved chromatographic separations for the desired products. The newly developed route mitigates the safety concerns, reduces the number of steps from five to three, avoids column chromatography, leads to an 8-fold improvement in yield, and utilizes reagents, which are recognized to be more environmentally benign.

Discovery of LOU064 (Remibrutinib), a Potent and Highly Selective Covalent Inhibitor of Bruton's Tyrosine Kinase

Bruton's tyrosine kinase (BTK), a cytoplasmic tyrosine kinase, plays a central role in immunity and is considered an attractive target for treating autoimmune diseases. The use of currently marketed covalent BTK inhibitors is limited to oncology indications based on their suboptimal kinase selectivity. We describe the discovery and preclinical profile of LOU064 (remibrutinib, 25), a potent, highly selective covalent BTK inhibitor. LOU064 exhibits an exquisite kinase selectivity due to binding to an inactive conformation of BTK and has the potential for a best-in-class covalent BTK inhibitor for the treatment of autoimmune diseases. It demonstrates potent in vivo target occupancy with an EC90 of 1.6 mg/kg and dose-dependent efficacy in rat collagen-induced arthritis. LOU064 is currently being tested in phase 2 clinical studies for chronic spontaneous urticaria and Sjoegren's syndrome.

Pyrazole spleen tyrosine kinase inhibitor as well as preparation method and application thereof

The invention discloses a pyrazole spleen tyrosine kinase inhibitor, a preparation method thereof, a pharmaceutical composition containing the same, and application of the pyrazole spleen tyrosine kinase inhibitor and the pharmaceutical composition in the preparation of drugs for treating Syk-mediated diseases including cancers, inflammatory diseases and the like.

Structural optimization and structure-activity relationship studies of N-phenyl-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-amine derivatives as a new class of inhibitors of RET and its drug resistance mutants

The RET tyrosine kinase is an important therapeutic target for medullary thyroid cancer (MTC), and drug resistance mutations of RET, particularly V804M and V804L, are a main challenge for the current targeted therapy of MTC based on RET inhibitors. In this investigation, we report the structural optimization and structure-activity relationship studies of N-phenyl-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazin-4-amine derivatives as a new class of RET inhibitors. Among all the obtained kinase inhibitors, 1-(5-(tert-butyl)isoxazol-3-yl)-3-(4-((6,7,8,9-tetrahydropyrimido[5,4-b][1,4]oxazepin-4-yl)amino)phenyl)urea (17d) is a multi-kinase inhibitor and potently inhibits RET and its drug resistance mutants. It showed IC50 (half maximal inhibitory concentration) values of 0.010 μM, 0.015 μM, and 0.009 μM against RET-wild-type, RET-V804M, and RET-V804L, respectively. 17d displayed significant anti-viability potencies against various RET-driving tumor cell lines. In a xenograft mouse model of NIH3T3-RET-C634Y, 17d exhibited potent in vivo anti-tumor activity, and no obvious toxicity was observed. Mechanisms of action were also investigated by Western blot and immunohistochemical assays. Collectively, 17d could be a promising agent for the treatment of MTC, hence deserving a further investigation.

Pyrimidomorpholine derivative, and preparation method and application thereof

The invention specifically relates to a small molecule compound capable of resisting medullary thyroid carcinoma, acute leukemia and inflammations, and a preparation method and application thereof, belonging to the field of chemical pharmaceuticals. The objective of the invention is to overcome the technical problems of poor selectivity, easy incurrence of drug resistance and toxic and side effectof conventional commercially-available clinical medicines for medullary thyroid carcinoma. The invention provides a pyrimidomorpholine derivative to overcome the above technical problem. The pyrimidomorpholine derivative is mainly characterized in that the position 6 of pyrimidine is substituted, and the structure of the pyrimidomorpholine is as shown in a formula I which is described in the specification. The compound provided by the invention has the advantages of high activity in resisting medullary thyroid carcinoma, low toxic and side effect and capacity of overcoming clinical drug resistance, and has great value in development of medicines for treating medullary thyroid carcinoma.

SUBSTITUTED NITROGEN-CONTAINING SIX-MEMBERED AMINO-HETEROCYCLES AS VANILLOID-1 RECEPTOR ANTAGONISTS FOR TREATING PAIN

The present invention provides a compound of formula (I): Y-J-NH-Z wherein: Y is a quinoline or isoquinoline optionally substituted with one or two substituents independently chosen from hydroxy, halogen, haloC1-4alkyl, C1-4alkyl, C1-4alkoxy, haloC1-4alkoxy, nitro and amino; J is pyridine, pyridazine, pyrazine, pyrimidine or triazine optionally substituted with one or two substituents independently chosen from hydroxy, halogen, haloC1-4alkyl, C1-4alkyl, C3-5cycloalkyl, C1-4alkoxy, hydroxyC1-4alkyl, cyano, hydroxy, C1-4cycloalkoxy, C1-4alkylthio, haloC1-4alkoxy, nitro, Q, (CH2)pQ, NR2R3, -(CH2)pNR2R3 and -O(CH2)pNR2R3; wherein J is substituted at positions meta to each other by NH and Y; and Z is phenyl or pyridyl optionally substituted with one or two substituents independently selected from halogen, haloC1-4alkyl, C1-4alkyl, C1-4alkoxy, haloC1-4alkoxy, nitro and amino; Q is phenyl, a five-membered heterocyclic ring containing one, two, three or four heteroatoms chosen from O, N and S, at most one heteroatom being O or S, or a six-membered heterocyclic ring containing one, two or three nitrogen atoms, optionally substituted by C1-4alkyl; each R2 and R3 is chosen from H and C1-4alkyl, or R2 and R3, together with the nitrogen atom to which they are attached, may form a six-membered ring optionally containing an oxygen atom or a further nitrogen atom, which ring is optionally substituted by C1-4alkyl or Q; p is 1, 2 or 3; or a pharmaceutically acceptable salt thereof; pharmaceutical compositions comprising it; its use in methods of therapy; use of it for manufacturing medicaments; and methods of using it to treat diseases requiring administration of a VR1 antagonist such as pain, cough, GERD and depression.