112342-72-0

Basic information

• Product Name: 2-AMINO-6-BROMOTHIAZOLO[4,5-B]PYRAZINE
• Synonyms: 2-AMINO-6-BROMOTHIAZOLO[4,5-B]PYRAZINE
• CAS NO: 112342-72-0
• Molecular Formula: C5H3BrN4S
• Molecular Weight: 231.08
• Mol File: 112342-72-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 366℃
• Flash Point: 175℃
• Appearance: /
• Density: 2.078
• Vapor Pressure: 1.51E-05mmHg at 25°C
• Refractive Index: 1.826
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: -3.63±0.50(Predicted)
• CAS DataBase Reference: 2-AMINO-6-BROMOTHIAZOLO[4,5-B]PYRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-6-BROMOTHIAZOLO[4,5-B]PYRAZINE(112342-72-0)
• EPA Substance Registry System: 2-AMINO-6-BROMOTHIAZOLO[4,5-B]PYRAZINE(112342-72-0)

Safety Data

• Hazardous Substances Data: 112342-72-0(Hazardous Substances Data)

Usage

Uses

2-Amino-6-bromothiazolo[4,5-b]pyrazine is derived from 2-Amino-3,5-dibromopyrazine (A604635), which is used in the preparation of conjugated polymers for neurotoxin detection and is an intermediate in the preparation of rho kinase (ROCK) inhibitors.

InChI:InChI=1/C5H3BrN4S/c6-2-1-8-3-4(9-2)11-5(7)10-3/h1H,(H2,7,8,10)

Upstream product

• 112342-71-9 2-aminothiazolo/4,5-b/pyrazine 
• 24241-18-7 2-amino-3,5-dibromopyrazine 
• 112342-69-5 2-ethoxycarbonylaminothiazolo/4,5-b/pyrazine 
• 56406-73-6 ethyl[(pyrazin-2-ylamino)carbonothioyl]carbamate 
• 112342-70-8 6-bromo-2-ethoxycarbonylaminothiazolo/4,5-b/pyrazine 

Relevant articles and documents

Solid-Phase Parallel Synthesis of N-Substituted-2-aminothiazolo[4,5-b]pyrazine Derivatives via Tandem Reaction of Isothiocyanate Terminated Resin with o-Bromo-2-Aminopyrazines

A novel solid-phase synthesis methodology of N-substituted-2-aminothiazolo[4,5-b]pyrazine derivatives was developed. The key step in this synthesis strategy is the tandem reaction of isothiocyanate terminated resin 2 with o-bromo-2-aminopyrazine, affording cyclized 2-aminothiazolo[4,5-b]pyrazine resin 4. To increase the diversity of our library, Suzuki coupling reaction was performed at the position C6. Further functionalization of 2-aminothiazolo[4,5-b]pyrazine core skeleton with various electrophiles such as alkyl halides, acyl chlorides, and sulfonyl chlorides and cleavage from the resin with TFA in DCM generated N-alkyl-, N-acyl-, and N-sulfonyl-2-aminothiazolo[4,5-b]pyrazine derivatives. The physicochemical properties and the polar surface areas of synthesized compounds were evaluated.

TRANSFORMATIONS OF 1,2,4-THIADIAZOLO/2,3-x/AZINES

Hydrolysis of 1,2,4-thiadiazolo/2,3-c/pyrimidine derivative 2 produced cyanoaminopyrimidine 4, while treatment of 1,2,4-thiadiazolo/2,3-b/pyridazine 5 with hydrazine hydrate gave thiourea derivative 7. 1,2,4-Thiadiazolo/2,3-a/pyridine 8 and 1,2,4-thiadiazolo/2,3-a/pyrazine 9 gave by alkaline hydrolysis the corresponding pyridopyrimidine 10 and pteridine 11, respectively.The compound 10 was converted with phenacyl bromide into 14 and further cyclized in PPA into pyrido/2,3-d/thiazolo/2,3-a/pyrimidine 15.Pyrazinylthiourea derivative 16 was cyclized in acidic solution into thiazolo/4,5-b/pyrazine 17, which was converted by hydrolysis and decarboxylation into amino derivative 20.This gave with ethyl acetoacetate pyrazino/2',3':4,5/thiazolo/3,2-a/pyrimidine 23. 1,2,4-Thiadiazoloazines 24 and N-ethoxycarbonyl-N'-azinylthioureas 25 were transformed with hydrogen peroxide into urea derivatives 26.