55583-59-0

Usage

Uses

Used in Chemical Synthesis:
2,5-Diamino-4,6-dichloropyrimidine is used as a building block in chemical synthesis. Its versatile structure allows it to be a key component in the creation of more complex molecules, particularly in the pharmaceutical and chemical industries. Its reactivity and functional groups make it a valuable intermediate for the synthesis of various compounds.
Used in Pharmaceutical Industry:
2,5-Diamino-4,6-dichloropyrimidine is used as a useful reagent for the preparation of Abacavir impurities, carbocyclic, and hexenopyranosy nucleosides. These compounds are essential in the development of new drugs and therapies, particularly in the treatment of viral infections and other diseases. 2,5-Diamino-4,6-dichloropyrimidine's role in pharmaceutical synthesis highlights its importance in the development of novel medications and treatments.

InChI:InChI=1/C4H4Cl2N4/c5-2-1(7)3(6)10-4(8)9-2/h7H2,(H2,8,9,10)

Upstream product

• 56830-58-1 2,5-diamino-4,6-dihydroxypyrimidine hydrochloride 
• 180330-54-5 water ethanol 
• 171887-01-7 2,5-bis{[(dimethylamino)methylene]amino}-4,6-dichloropyrimidine 
• 10052-47-8 triethylmethylammonium chloride 
• 56830-58-1 2,5-Diamino-4,6-dihydroxypyrimidine hydrochloride 
• 40215-83-6 N-ethyl-N-methyl piperidinium chloride 
• 96-18-4 1,2,3-trichloropropane 
• 171887-03-9 N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide 
• 91322-00-8 5-amino-2,4,6-trichloropyrimidine 

Downstream Products

• 186416-92-2 2,5-diamino-4-benzylamino-6-chloropyrimidine 
• 171887-03-9 N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide 
• 141271-12-7 (1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol 
• 848696-40-2 6-chloro-N₄-(3,4,5-trimethoxy-benzyl)-pyrimidine-2,4,5-triamine 
• 6270-25-3 4-Chlor-2,5-diamino-6-butylamino-pyrimidin 
• 1187205-77-1 4-chloro-6-(4-methoxyphenyl)-pyrimidine-2,5-diamine 
• 1040353-75-0 2-amino-4-chloro-6-(3-methyl-4-nitro-benzylamino)-pyrimidin-5-yl-amine 
• 1037397-92-4 7-chloro-3-(3-methyl-4-nitro-benzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ylamine 
• 131853-53-7 2,5-diamino-6-chloro-4-<<3,3-bis(benzyloxymethyl)cyclobut-1-yl>amino>pyrimidine 
• 128631-58-3 (+/-)-2,5-diamino-6-chloro-4-<<5-(benzyloxy)-3-hydroxypent-1-yl>amino>pyrimidine 
• 50619-39-1 (+/-)-2,5-diamino-4-N-<2α,3β-dihydroxy-4α-(hydroxymethyl)cyclopent-1α-yl>amino-6-chloropyrimidine 
• 131853-60-6 2,5-diamino-6-chloro-4-<(cyclohex-3-en-1-yl)amino>pyrimidine 
• 116477-30-6 4,6-dichloro-2,5-diformamido-pyrimidine 
• 1044243-97-1 2-amino-4-chloro-8-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7,8-dihydropteridin-6(5H)-one 

Relevant academic research and scientific papers

Triazolopyrimidines identified as reversible myeloperoxidase inhibitors

Myeloperoxidase, a mammalian peroxidase involved in the immune system as an anti-microbial first responder, can produce hypochlorous acid in response to invading pathogens. Myeloperoxidase has been implicated in several chronic pathological diseases due to the chronic production of hypochlorous acid, as well as other reactive radical species. A high throughput screen and triaging protocol was developed to identify a reversible inhibitor of myeloperoxidase toward the potential treatment of chronic diseases such as atherosclerosis. The identification and characterization of a reversible myeloperoxidase inhibitor, 7-(benzyloxy)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-amine is described.

ANTI-CANCER ACTIVITY OF NOVEL BICYCLIC HETEROCYCLES

The present invention relates to compound of formula I, II, III, or IV, and/or a pharmaceutical acceptable addition salt thereof and/or a stereoisomer thereof and/or a solvate thereof, Formulas (I), (II), (III) and (IV) wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R11, and R12 are as defined in the claim 1 or as described in detail in the description of the invention, and to the use of said compounds to treat or prevent proliferative disorders and their use to manufacture a medicine to treat or prevent proliferative disorders, particularly cancer such as leukemia. The present invention also relates to pharmaceutical compositions of said compounds and the use of said pharmaceutical compositions to treat or prevent proliferative disorders. The present invention further relates to the use of said compounds as biologically active ingredients, more specifically as medicaments for the treatment of proliferative disorders and pathologic conditions such as, but not limited to, cancer such as leukemia.

Antiviral Activity of Novel Bicyclic Heterocycles

The present invention relates to compound of Formula I, II, III, or IV, and/or a pharmaceutical acceptable addition salt thereof and/or a stereoisomer thereof and/or a solvate thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R11, and R12 are as defined in the claim 1 or as described in detail in the description of the invention, and to the use of said compounds to treat or prevent viral infections and their use to manufacture a medicine to treat or prevent viral infections, particularly infections with RNA-viruses belonging to the family of the Retroviridae, the family of the Flaviviridae and the family of the Picornaviridae and more preferably infections with Human Immunodeficiency Virus 1 (HIV1), Human Immunodeficiency Virus 2 (HIV2), Hepatitis C virus (HCV), Dengue virus, and enteroviruses like Coxsackievirus, Rhinovirus and Poliovirus. The present invention also relates to pharmaceutical compositions of said compounds and the use of said pharmaceutical compositions to treat or prevent viral infections. The present invention further relates to the use of said compounds as biologically active ingredients, more specifically as medicaments for the treatment of viral disorders and pathologic conditions such as, but not limited to, viral infections with Human Immunodeficiency Virus 1 (HIV1), Human Immunodeficiency Virus 2 (HIV2), Hepatitis C virus (HCV), Dengue virus, and enteroviruses like Coxsackievirus, Rhinovirus and Poliovirus.

THIAZOLOPYRIMIDINE MODULATORS AS IMMUNOSUPPRESSIVE AGENTS

The present invention relates to compound of formula I, II, III, or IV, and/or a pharmaceutical acceptable addition salt thereof and/or a stereoisomer thereof and/or a solvate thereof, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R11, and R12 are as defined in the claim 1. The present invention also relates to a method for their preparation, as well as to pharmaceutical compositions thereof. The present invention further relates to the use of said compounds as biologically active ingredients, more specifically as medicaments for the treatment of disorders and pathologic conditions such as, but not limited to, immune and auto-immune disorders, organ and cells transplant rejections.

Discovery of 7- N -piperazinylthiazolo[5,4- d ]pyrimidine analogues as a novel class of immunosuppressive agents with in vivo biological activity

Herein we describe the synthesis and in vitro and in vivo activity of thiazolo[5,4-d]pyrimidines as a novel class of immunosuppressive agents, useful for preventing graft rejection after organ transplantation. This research resulted in the discovery of a series of compounds with potent activity in the mixed lymphocyte reaction (MLR) assay, which is well-known as the in vitro model for in vivo rejection after organ transplantation. The most potent congeners displayed IC50 values of less than 50 nM in this MLR assay and hence are equipotent to cyclosporin A, a clinically used immunosuppressive drug. One representative of this series was further evaluated in a preclinical animal model of organ transplantation and showed excellent in vivo efficacy. It validates these compounds as new promising immunosuppressive drugs.

Process for the preparation of 2,5-diamino-4,6-dihalogenopyrimidinen

A halogenated hydrocarbon solvent is used in the production of 2,5-diamino-4,6-dihalo-pyrimidines (I) by reaction of 2,5-diamino-4,6-dihydroxy-pyrimidine (II) or its salts with a phosphorus oxyhalide and a quaternary ammonium halide. A halogenated hydrocarbon solvent is used in the production of 2,5-diamino-4,6-dihalo-pyrimidines of formula (I) by reaction of 2,5-diamino-4,6-dihydroxy-pyrimidine of formula (II) or its salts with a phosphorus oxyhalide and a quaternary ammonium halide. X = halo.

Process for the preparation of N-(amino-4,6-dihalo-pyrimidine) formamides

A process for the preparation of N-(amino-4,6-dihalopyrimidine)formamides of the formula: in which X is a halogen atom, starting from 2,5-diamino-4,6-dihalopyrimidine of the formula: in which X has the meaning afore-mentioned, by reaction with formic acid.

An efficient, scalable synthesis of the HIV reverse transcriptase inhibitor Ziagen (1592U89)

Ziagen, (1S, cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2- cyclopentene-1-methanol, was synthesized from (1S,4R)-azabicyclo[2.2.1]hept- 5-en-3-one by efficient processes which bypass problematic steps in earlier routes. 2-Amino-4,6-dichloro-5-formamidopyrimidine is a key intermediate which makes possible an efficient construction of the purine from a chiral cyclopentenyl precursor.

Chloropyrimidine intermediates

The present invention is related to a process of making of 2,6-diaminopurines wherein the 6-amino group is substituted by R4 and R5, by reacting a compound of formula (VI) STR1 with an excess of amine NHR4 R5.

Process for preparing 2,5-diamino-4,6-dichloropyrimidine

A process for the preparation of 2,5-diamino-4,6-dichloropyrimidine, which process comprises the chlorination of 2,5-diamino-4,6-dihydroxypyrimidine with phosphorus oxychloride and a quaternary ammonium chloride or a weak tertiary amine base hydrochloride.