13479-88-4

Basic information

• Product Name: 5,7-dichlorothiazolo[5,4-d]pyrimidine
• Synonyms: 5,7-dichlorothiazolo[5,4-d]pyrimidine;5,7-dichloro-[1,3]thiazolo[5,4-d]pyriMidine
• CAS NO: 13479-88-4
• Molecular Formula: C₅HCl₂N₃S
• Molecular Weight: 206.05
• Product Categories: Heterocycle-Pyrimidine series
• Mol File: 13479-88-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 148.5-149.5 °C
• Boiling Point: 281.2 °C at 760 mmHg
• Flash Point: 123.9 °C
• Appearance: /
• Density: 1.767 g/cm³
• Vapor Pressure: 0.00615mmHg at 25°C
• Refractive Index: 1.73
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -2.68±0.50(Predicted)
• CAS DataBase Reference: 5,7-dichlorothiazolo[5,4-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-dichlorothiazolo[5,4-d]pyrimidine(13479-88-4)
• EPA Substance Registry System: 5,7-dichlorothiazolo[5,4-d]pyrimidine(13479-88-4)

Safety Data

• Hazardous Substances Data: 13479-88-4(Hazardous Substances Data)

Usage

Uses

5,7-Dichlorothiazolo[5,4-d]pyrimidine was used in studies to prepare Kinase inhibitors.

InChI:InChI=1/C5HCl2N3S/c6-3-2-4(11-1-8-2)10-5(7)9-3/h1H

Upstream product

• 5082-82-6 4H-thiazolo[5,4-d]pyrimidine-5,7-dione 
• 1394941-05-9 ethyl 5-((ethoxycarbonyl)amino)thiazole-4-carboxylate 
• 5021-69-2 (4-carbamoylthiazol-5-yl)carbamic acid ethyl ester 
• 5082-82-6 thiazolo[5,4-d]pyrimidine-5,7-(4H,6H)-dione 

Downstream Products

• 1401461-83-3 (5-chlorothiazolo[5,4-d]pyrimidin-7-yl)-(3,4-dimethoxyphenyl)amine 
• 1401462-47-2 5-chloro-N-(3-(trifluoromethyl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine 
• 1401462-48-3 5-chloro-N-(3,4,5-trimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine 
• 1401461-05-9 3-[7-(3,4-dimethoxy-phenylamino)-thiazolo[5,4-d]pyrimidin-5-yl]-benzoic acid 
• 1401461-08-2 4-{3-[7-(3,4-Dimethoxy-phenylamino)-thiazolo[5,4-d]pyrimidin-5-yl]-benzoylamino}-benzoic acid 
• 1401461-28-6 4-[7-(3,4-Dimethoxy-phenylamino)-thiazolo[5,4-d]pyrimidin-5-yl]-N-(2-pyridin-4-yl-ethyl)-benzamide 
• 1401461-31-1 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(2-(2-oxo-1,2-dihydropyridin-4-yl)ethyl)piperidine-4-carboxamide 
• 1401461-32-2 4-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(2-(2-oxo-1,2-dihydropyridin-4-yl)ethyl)benzamide 
• 1401461-33-3 4-[7-(3,4-Dimethoxy-phenylamino)-thiazolo[5,4-d]pyrimidin-5-yl]-N-[2-(1-methyl-2-oxo-1,2-dihydro-pyridin-4-yl)-ethyl]-benzamide 
• 1401461-34-4 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(2-(pyridin-4-yl)ethyl)piperidine-3-carboxamide 
• 1401461-40-2 tert-butyl 4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzylamino)benzoate 
• 1401461-43-5 (E)-4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)styryl)benzoic acid 
• 1401461-44-6 4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)phenethyl)benzoic acid 
• 1401461-61-7 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(pyrazin-2-yl)piperidine-3-carboxamide 

Relevant articles and documents

SUBSTITUTED BICYCLIC PYRIMIDINE-BASED COMPOUNDS AND COMPOSITIONS AND USES THEREOF

Novel C-2-substituted bicyclic compounds of Formula I have been prepared and found to be useful as potent inhibitors of hGGPPS by inhibiting geranylgeranylation of proteins and inhibiting the biosynthesis of GGPP. The application is directed to these compounds, to compositions comprising these compounds, and to their use, in particular as medicaments for use in the treatment of cancer and other conditions which are treatable by inhibiting human geranylgeranylation pyrophosphate hGGPPS activity.

Discovery of a First-in-Class, Potent, Selective, and Orally Bioavailable Inhibitor of the p97 AAA ATPase (CB-5083)

The AAA-ATPase p97 plays vital roles in mechanisms of protein homeostasis, including ubiquitin-proteasome system (UPS) mediated protein degradation, endoplasmic reticulum-associated degradation (ERAD), and autophagy. Herein we describe our lead optimization efforts focused on in vitro potency, ADME, and pharmaceutical properties that led to the discovery of a potent, ATP-competitive, D2-selective, and orally bioavailable p97 inhibitor 71, CB-5083. Treatment of tumor cells with 71 leads to significant accumulation of markers associated with inhibition of UPS and ERAD functions, which induces irresolvable proteotoxic stress and cell death. In tumor bearing mice, oral administration of 71 causes rapid accumulation of markers of the unfolded protein response (UPR) and subsequently induces apoptosis leading to sustained antitumor activity in in vivo xenograft models of both solid and hematological tumors. 71 has been taken into phase 1 clinical trials in patients with multiple myeloma and solid tumors.

Convenient synthesis of 5,7-dichlorothiazolo[5,4-d]pyrimidine

A convenient synthesis of 5,7-dichlorothiazolo[5,4-d]pyrimidine is reported. The condensation of ethyl isocyanoacetate and ethoxycarbonyl isothiocyanate selectively gave the key 5-aminothiazole intermediate in high yield under mild conditions. This interm