35265-83-9

Basic information

• Product Name: 2,4-Dichloro-7-methylthieno[3,2-d]pyrimidine
• Synonyms: 2,4-Dichloro-7-methylthieno[3,2-d]pyrimidine;Thieno[3,2-d]pyriMidine, 2,4-dichloro-7-Methyl-;2,4-Dichloro-7-methylthieno[3,2-d]pyrimidine-3
• CAS NO: 35265-83-9
• Molecular Formula: C₇H₄Cl₂N₂S
• Molecular Weight: 219.09
• Product Categories: Heterocycle-Pyrimidine series
• Mol File: 35265-83-9.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 293℃
• Flash Point: 131℃
• Appearance: /
• Density: 1.568
• Vapor Pressure: 0.00308mmHg at 25°C
• Refractive Index: 1.688
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.48±0.40(Predicted)
• CAS DataBase Reference: 2,4-Dichloro-7-methylthieno[3,2-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichloro-7-methylthieno[3,2-d]pyrimidine(35265-83-9)
• EPA Substance Registry System: 2,4-Dichloro-7-methylthieno[3,2-d]pyrimidine(35265-83-9)

Safety Data

• Hazardous Substances Data: 35265-83-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dichloro-7-methylthieno[3,2-d]pyrimidine is used as a building block in the synthesis of pharmaceuticals for its ability to form complex molecular structures with potential therapeutic effects. Its unique chemical composition allows it to be a versatile component in the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical sector, 2,4-Dichloro-7-methylthieno[3,2-d]pyrimidine serves as an intermediate in the production of various agrochemicals, contributing to the development of effective pest control agents and other agricultural products.
Used in Dye and Pigment Production:
2,4-Dichloro-7-methylthieno[3,2-d]pyrimidine is utilized as an intermediate in the manufacturing process of dyes and pigments, where its specific chemical properties enable the creation of a wide range of colorants for different applications.
Used in Organic Compound Synthesis:
2,4-Dichloro-7-methylthieno[3,2-d]pyrimidine is employed as an intermediate in the synthesis of other organic compounds, showcasing its versatility and importance in organic chemistry.
Used in Medicinal Chemistry Research:
2,4-Dichloro-7-methylthieno[3,2-d]pyrimidine holds potential applications in medicinal chemistry, as it is under research for its biological properties and therapeutic uses, indicating its significance in the discovery of novel treatments and pharmaceutical agents.

InChI:InChI=1/C7H4Cl2N2S/c1-3-2-12-5-4(3)10-7(9)11-6(5)8/h2H,1H3

Upstream product

• 35265-81-7 7-methylthieno[3,2-d]pyrimidine-2,4-diol 
• 85006-31-1 3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester 
• 57-13-6 urea 
• 35265-81-7 7-methylthieno<3,2-d>pyrimidine-2,4-dione 

Downstream Products

• 221043-63-6 2-Chloro-4-(trans-cinnamylamino)-7-methylthieno[3,2-d] pyrimidine 
• 35265-88-4 4-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)morpholine 
• 1356016-35-7 2-chloro-thieno[3,2-d]pyrimidine-7-carbaldehyde 
• 1356017-09-8 2-Chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (3,4-dimethoxy-phenyl)-amide 
• 1356017-78-1 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (3,4,5-trimethoxy-phenyl)-amide 
• 955979-02-9 2-chloro-7-methyl-4-morpholinothieno[3,2-d]-pyrimidine-6-carbaldehyde 
• 1356017-12-3 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid(2,4-dimethoxy-phenyl)-amide 
• 1024603-90-4 2-chloro-4-(mesityloxy)-7-methylthieno[3,2-d]pyrimidine 
• 221043-41-0 2-Chloro-4-cyclohexylamino-7-methylthieno[3,2-d] pyrimidine 
• 221043-39-6 4-benzylamino-2-chloro-7-methylthieno[3,2-d]pyrimidine 

Relevant articles and documents

ECTONUCLEOTIDE PYROPHOSPHATASE/PHOSPHODIESTERASE 1 (ENPP1) MODULATORS AND USES THEREOF

Provided herein are small molecule modulators of ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1), compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.

Discovery of novel and potent PARP/PI3K dual inhibitors for the treatment of cancer

PARP inhibitors have achieved great success in cancers with BRCA mutations, but only a small portion of patients carry BRCA mutations, which results in their narrow indication spectrum. Recently, emerging evidence has demonstrated that combinations of PARP and PI3K inhibitors could evoke unanticipated synergistic effects in various cancers, even including BRCA-proficient ones. In this work, a series of PARP/PI3K dual inhibitors were designed, synthesized, and evaluated for their biological activities. It was found that compounds 9a and 23a exhibited excellent inhibitory activities against PARP-1 (9a: IC50 = 1.57 nM, 23a: IC50 = 0.91 nM) and PI3Kα (9a: IC50 = 2.0 nM, 23a: IC50 = 1.5 nM), and showed promising antiproliferative activities against both BRCA-deficient (HCT-116, HCC-1937) and BRCA-proficient (SW620, MDA-MB-231/468) tumor cells. 9a and 23a also exhibited considerable in vivo antitumor efficacy in an MDA-MB-468 xenograft mouse model, with TGI values of 56.39% and 48.77%, respectively. Additionally, 23a possessed promising profiles including high kinase selectivity and low cardiotoxicity. Overall, this work indicates 9a and 23a might be potential PARP/PI3K dual inhibitors for cancer therapy and deserve further research.

PYRIMIDINE AMIDE COMPOUNDS AND USE THEREOF

Disclosed are compounds of formula (I) below or a stereoisomer, a tautomer, or a pharmaceutically acceptable salt thereof: (I), in which each of variables each of variables R, R1, R2, X1, X2, X3 and n is defined herein. Also disclosed is a method for treating a cancer with a compound of formula (I) or a salt thereof and a pharmaceutical composition containing same.

PARP-1/PI3K double-target inhibitor or pharmaceutically acceptable salt thereof, preparation method and application thereof

The invention discloses a PARP-1/PI3K double-target inhibitor or a pharmaceutically acceptable salt thereof, a preparation method and application thereof. According to the invention, the single active component can play a dual inhibition role on PARP-1 and PI3K, so that the dosage is reduced, the treatment effect is improved, and the toxic and side effects are reduced; and the dual inhibition effect on PARP-1 and PI3K is significant, the IC50 value of each target does not exceed 1.0 [mu]M, and the drug using the PARP-1/PI3K double-target inhibitor as the active component can be used for treating a variety of cancers or tumors related to PARP-1 and/or PI3K.

Discovery of an Orally Active and Long-Acting DPP-IV Inhibitor through Property-Based Optimization with an in Silico Biotransformation Prediction Tool

Long-acting dipeptidyl peptidase IV inhibitors have emerged as promising molecules for interventions for type 2 diabetes. Once weekly dosing brings greater patient compliance and more stable glycemic control. Starting from our previous highly potent compound with a thienoprimidine scaffold, which is unfortunately severely hit by hepatic biotransformation, a lead compound was rapidly generated by drawing on the experience of our previously discovered long-acting compounds with pyrrolopyrimidine scaffold. With the aid of an in silico biotransformation prediction tool, (R)-2-((2-(3-aminopiperidin-1-yl)-4-oxo-6-(pyridin-3-yl)thieno[3,2-d]pyrimidin-3(4H)-yl)methyl)-4-fluorobenzonitrile was eventually generated and determined to have high potency, a fine pharmacokinetic profile, and a long-acting in vivo efficacy.

Thienopyrimidinone compound or pharmaceutically-acceptable salt thereof and preparation method and application thereof

The invention provides a thienopyrimidinone compound or pharmaceutically-acceptable salt thereof and a preparation method and application thereof. The thienopyrimidinone compound or the pharmaceutically-acceptable salt thereof has a novel chemical structure, it is verified through in-vitro and in-vivo experiments that a very good selective inhibiting effect on DPP-IV is achieved, the activity of DPP-VIII and DPP-IX is barely affected while the activity of DPP-IV is effectively inhibited, meanwhile, the inhibition ratio of a potassium ion channel is low, and it can be predicted that the toxicity is low after the compound is developed into medicine. Compared with medicine trelagliptin orally taken once every week on the market, the thienopyrimidinone compound has fairly high or higher bioavailable efficiency, it can be predicted that after the compound is developed, the treatment effect that the compound is orally taken once for a long time, and the convenience and compliance of a patient are greatly improved. The preparation method is simple, the raw materials are easy to obtain, and the preparation method is suitable for industrial large-scale production.

Discovery of dual Axl/VEGF-R2 inhibitors as potential anti-angiogenic and anti-metastatic drugs for cancer chemotherapy

Axl tyrosine kinase has been shown to be involved in multiple pathways contributing to tumor development, angiogenesis, and metastasis. High Axl expression has been observed in many human tumors where it appears to confer aggressive tumor behavior. Here we present several series of dual Axl-VEGF-R2 kinase inhibitors based on extensive optimization of an acyl diaminotriazole. It was hypothesized that dual inhibition of these two receptor tyrosine kinases may have a synergistic affect in inhibiting tumor angiogenesis and metastasis. One of these molecules, R916562 showed comparable activity to Sunitinib in two mouse tumor xenograft models and a mouse corneal micropocket model.

PROCESS FOR MAKING THIENOPYRIMIDINE COMPOUNDS

Process methods for making the dual mTOR/PI3K inhibitor GDC-0980, named as (S)-1-(4-((2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)piperazin-1-yl)-2-hydroxypropan-1-one, having the structure: and stereoisomers, geometric isomers, tautomers, and pharmaceutically acceptable salts thereof.

THIENYL [3,2-D] PYRIMIDIN-4-ONE COMPOUNDS, PREPARATION METHOD, PHARMACEUTICAL COMPOSITIONS AND USE THEREOF

Disclosed are new thienyl[3,2-d]pyrimidin-4-one compounds shown as the general formula (I), preparation method, pharmaceutical compositions and pharmacological use thereof. The compounds are strong DPPIV (dipeptide peptidase IV) inhibitors and can treat t

PYRAZOLO[1,5a]PYRIMIDINE DERIVATIVES AS IRAK4 MODULATORS

Compounds of the formula I or II: wherein X, m, Ar, R1 and R2 are as defined herein. The subject compounds are useful for treatment of IRAK-mediated conditions.