37660-22-3

Basic information

• Product Name: 6-amino-2-(ethylthio)-1H-pyrimidin-4-one
• Synonyms: 6-amino-2-(ethylthio)-1H-pyrimidin-4-one;6-Amino-2-(ethylthio)pyrimidin-4(1H)-one;6-Amino-2-ethylthio-4-pyrimidinol;6-Amino-2-ethylsulfanyl-pyrimidin-4-ol;6-amino-2-(ethylsulfanyl)-3,4-dihydropyrimidin-4-one
• CAS NO: 37660-22-3
• Molecular Formula: C₆H₉N₃OS
• Molecular Weight: 171.22016
• EINECS: 253-579-9
• Mol File: 37660-22-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 297.2 °C at 760 mmHg
• Flash Point: 133.5 °C
• Appearance: /
• Density: 1.45 g/cm³
• Vapor Pressure: 0.00137mmHg at 25°C
• Refractive Index: 1.673
• CAS DataBase Reference: 6-amino-2-(ethylthio)-1H-pyrimidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-amino-2-(ethylthio)-1H-pyrimidin-4-one(37660-22-3)
• EPA Substance Registry System: 6-amino-2-(ethylthio)-1H-pyrimidin-4-one(37660-22-3)

Safety Data

• Hazardous Substances Data: 37660-22-3(Hazardous Substances Data)

Usage

General Description

The chemical compound 6-amino-2-(ethylthio)-1H-pyrimidin-4-one, also known as ET-743 or trabectedin, is a natural product derived from the sea squirt Ecteinascidia turbinate. It is a potent antitumor agent with unique mechanisms of action, including the binding to the minor groove of DNA and the inhibition of DNA repair processes. ET-743 has shown promising results in the treatment of various cancers, including soft tissue sarcoma and ovarian cancer. Its complex structure and mechanism of action make it a subject of ongoing research and clinical trials for potential applications in cancer therapy.

InChI:InChI=1/C6H9N3OS/c1-2-11-6-8-4(7)3-5(10)9-6/h3H,2H2,1H3,(H3,7,8,9,10)

Upstream product

• 1004-40-6 6-Amino-2-thiouracil 
• 64-67-5 diethyl sulfate 
• 74-96-4 ethyl bromide 
• 1004-40-6 4-aminothiouracil 
• 75-03-6 ethyl iodide 

Relevant articles and documents

Convenient One-Pot Four-Component Synthesis of 6,8-Disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]-pyrimidin-4(3H)-ones via a Triple Mannich Reaction

An efficient and simple one-pot four-component protocol has been developed and performed for the synthesis of 6,8-disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(3H)-ones, involving a triple Mannich reaction of 6-amino-2-(ethylthio)pyrimidin-4(3H)-one, formaldehyde, primary amines, and alcohols. Secondary amines were also utilised instead of alcohols as Mannich nucleophiles, and a variety of functional groups and electronically varied reaction partners were tolerated. This one-pot reaction facilitated the generation of a library of pyrimido[4,5-d]pyrimidin-4(3H)-ones in very good to excellent yields. The regioselectivity of this reaction was investigated using atomic charge calculations, and spectroscopic data confirmed that the triple Mannich products were 6,8-disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(3H)-ones rather than the isomeric 3,6-disubstituted-5,6,7,8-tetrahydropyrimido[4,5-d]pyrimidin-4(3H)-ones. The structures of all compounds synthesised using the triple Mannich reaction were confirmed via spectroscopic and elemental analyses. The reaction mechanism was studied and confirmed by isolation of the intermediate.

Chemical synthesis of some novel 6-aminouracil-2-thiones and their glycoside analogues

6-AMINOURACIL-2-THIONE (1) and its 5-bromo derivative 2 underwent alkylation yielding their respective S-alkyl products 4a-j. The reaction of compound 1 and aldehydes in the presence of chloroacetic acid afforded the respective thiazolopyrimidinyl acetamides 7a-d. The C-glycosides 8a, b and 9c-e were successfully prepared through condensing compound 1 and the appropriate sugar in the presence of chloroacetic acid. The behavior of certain S-alkyl derivative 4 towards amines and hydrazines was also studied. Structure elucidations for the new products were supported by compatible chemical and spectral measurements.

Hit-to-Lead studies: The discovery of potent, orally bioavailable thiazolopyrimidine CXCR2 receptor antagonists

A Hit-to-Lead optimisation programme was carried out on a high throughput screening hit, the thiazolopyrimidine 1, resulting in the discovery of the potent, orally bioavailable CXCR2 antagonist 29.