16234-14-3

Basic information

• Product Name: 2,4-Dichlorothieno[3,2-d]pyrimidine
• Synonyms: Thieno[3,2-d]pyrimidine, 2,4-dichloro-;2,4-Dichlorothiopheno[3,2-d]pyrimidine;2,4-dichlorothieno[3,2-d]pyrimidine ,97%;2,4-dichlorothieno[3,2-d]...;4-dichlorothieno[3;2,4-dichlorothieno;2,4-dichlorothieno[3,2-d]pgriMidine;2,4-Dichlorothieno[3,2-d]pyrimidine
• CAS NO: 16234-14-3
• Molecular Formula: C₆H₂Cl₂N₂S
• Molecular Weight: 205.06448
• EINECS: 1312995-182-4
• Product Categories: Heterocycles;API intermediates;CHIRAL CHEMICALS;Heterocycle-Pyrimidine series
• Mol File: 16234-14-3.mol
• Article Data: 77

Chemical Properties

• Melting Point: 136.0 to 140.0 °C
• Boiling Point: 274.804 °C at 760 mmHg
• Flash Point: 119.997 °C
• Appearance: /
• Density: 1.662 g/cm³
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: -0.72±0.40(Predicted)
• CAS DataBase Reference: 2,4-Dichlorothieno[3,2-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichlorothieno[3,2-d]pyrimidine(16234-14-3)
• EPA Substance Registry System: 2,4-Dichlorothieno[3,2-d]pyrimidine(16234-14-3)

Safety Data

• Safety Statements: 24/25
• RIDADR: UN2811
• HazardClass: IRRITANT
• Hazardous Substances Data: 16234-14-3(Hazardous Substances Data)

Usage

Description

2,4-Dichlorothieno[3,2-d]pyrimidine is an organic compound characterized by its white solid appearance. It is a heterocyclic compound with a unique chemical structure that features a thienopyrimidine ring system substituted with two chlorine atoms at the 2nd and 4th positions.

Uses

Used in Pharmaceutical Industry:
2,4-Dichlorothieno[3,2-d]pyrimidine is used as a key intermediate in the synthesis of PI3K inhibitors, which are important for the development of targeted cancer therapies. These inhibitors modulate the PI3K/AKT/mTOR signaling pathway, a crucial regulator of cell growth, survival, and metabolism, often dysregulated in various cancers. The compound's role in the synthesis process is to facilitate the creation of PI3K inhibitors under noncryogenic conditions, making the production process more efficient and cost-effective.

Upstream product

• 22288-78-4 Methyl 3-aminothiophene-2-carboxylate 
• 57-13-6 urea 
• 16233-51-5 2,4-dihydroxythieno[3,2-d]pyrimidine 
• 16233-51-5 thienoyleneurea 
• 16233-51-5 1H-thieno[3,2-d]pyrimidine-2,4-dione 
• 51322-68-0 methyl 3-[(aminocarbonyl)amino]-2-thiophenecarboxylate 

Downstream Products

• 16234-15-4 2-chloro-4-morpholinothieno[3,2-d]pyrimidine 
• 885698-98-6 4-(6-(bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine 
• 885675-66-1 4-(2-chloro-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)thieno[3,2-d]-pyrimidin-4-yl)morpholine 
• 1235450-27-7 Ethyl 2-((2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methylamino)pyrimidine-5-carboxylate 
• 1235450-94-8 methyl 2-(((2-(4-(aminomethyl)phenyl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)(methyl)amino)pyrimidine-5-carboxylate 
• 1235450-97-1 methyl 2-(((2-(3-(aminomethyl)phenyl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)(methyl)amino)pyrimidine-5-carboxylate 
• 1235451-07-6 ethyl 2-(((2-(4-aminophenyl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)(methyl)amino)pyrimidine-5-carboxylate 
• 1235451-15-6 ethyl 2-(((2-chloro-4-(phenylamino)thieno[3,2-d]pyrimidine-6-yl)methyl)(methyl)amino)pyrimidine-5-carboxylate 
• 1235450-95-9 ethyl 2-(((2-(4-(acetamidomethyl)phenyl)-4-morpholinothieno[3,2-d]pyrimidine-6-yl)Methyl)(methyl)amino)pyrimidine-5-carboxylate 
• 1235450-96-0 2-(((2-(4-(aminomethyl)phenyl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)(methyl)amino)pyrimidine-5-carboxylic acid 
• 1235450-98-2 ethyl 2-(((2-(3-(acetamidomethyl)phenyl)-4-morpholinothieno[3,2-d]pyrimidine-6-yl)Methyl)(methyl)amino)pyrimidine-5-carboxylate 
• 1235450-99-3 2-(((2-(3-(aminomethyl)phenyl)-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)(methyl)amino)pyrimidine-5-carboxylic acid 
• 1235451-08-7 ethyl 2-(((2-(4-acetamidophenyl)-4-morpholinothieno-[3,2-d]pyrimidin-6-yl)methyl)(methyl)amino)pyrimidine-5-carboxylate 

Relevant articles and documents

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.

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.

Design, synthesis and biological evaluation of novel 2,4-bismorpholinothieno[3,2-d]pyrimidine and 2-morpholinothieno[3,2-d]pyrimidinone derivatives as potent antitumor agents

To develop novel therapeutic agents with anticancer activities, two series of novel 2,4-bismorpholinyl-thieno[3,2-d]pyrimidine and 2-morpholinothieno[3,2-d]pyrimidinone derivatives were designed, synthesized and evaluated for their biological activities. Among them, compound A12 showed the most potent antitumor activities against HCT116, PC-3, MCF-7, A549 and MDA-MB-231 cell lines with IC50 values of 3.24 μM, 14.37 μM, 7.39 μM, 7.10 μM, and 16.85 μM, respectively. Further explorations in bioactivity were conducted to clarify the anticancer mechanism of compound A12. The results showed that compound A12 obviously inhibited the proliferation of A549 cell lines and decreased mitochondrial membrane potential, which led to the apoptosis of cancer cells and suppressed the migration of tumor cells.