5-Hydroxy-3-methylpyridine-2-carbonitrile

Base Information

• Chemical Name: 5-Hydroxy-3-methylpyridine-2-carbonitrile
• CAS No.: 228867-86-5
• Molecular Formula: C₇H₆N₂O
• Molecular Weight: 134.137
• Hs Code.: 2933399090
• Mol file: 228867-86-5.mol

Synonyms:5-hydroxy-3-methylpyridine-2-carbonitrile;

Chemical Property of 5-Hydroxy-3-methylpyridine-2-carbonitrile

Chemical Property:

• Refractive Index: 1.578
• Boiling Point: 419.7 °C at 760 mmHg
• PKA: 3.36±0.23(Predicted)
• Flash Point: 207.6 °C
• PSA: 56.91000
• Density: 1.26 g/cm³
• LogP: 0.96728
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Hydroxy-3-methylpicolinonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-Hydroxy-3-methylpyridine-2-carbonitrile

There total 7 articles about 5-Hydroxy-3-methylpyridine-2-carbonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

5-amino-3-methylpyridine-2-carbonitrile (252056-70-5) → 5-hydroxy-3-methylpyridine-2-carbonitrile (228867-86-5)

Guidance literature:

With sulfuric acid; sodium nitrite; In water; at 0 - 100 ℃; for 3h;

Reference yield: 32.0%

zinc(II) cyanide (557-21-1) + 2-chloro-5-hydroxy-3-methylpyridine (54232-03-0) → 5-hydroxy-3-methylpyridine-2-carbonitrile (228867-86-5)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In N,N-dimethyl-formamide; at 110 ℃; for 21h; Inert atmosphere; Sealed tube;

Reference yield:

2-cyano-3-methylpyridine (20970-75-6) → 5-hydroxy-3-methylpyridine-2-carbonitrile (228867-86-5)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrabutylammonium nitrate; trifluoroacetic anhydride / tert-butyl methyl ether / 60 h / 4 - 20 °C

2: calcium chloride; iron / water; ethanol / 20 °C

3: sulfuric acid; sodium nitrite / water / 3 h / 0 - 100 °C

With sulfuric acid; tetrabutylammonium nitrate; iron; trifluoroacetic anhydride; calcium chloride; sodium nitrite; In ethanol; tert-butyl methyl ether; water;

upstream raw materials:

zinc(II) cyanide

2-chloro-5-hydroxy-3-methylpyridine

6-chloro-5-methylpyridin-3-amine

2-chloro-3-methyl-5-nitropyridine

Downstream raw materials:

3-methyl-5-(2,2,2-trifluoroethoxy)picolinonitrile

(S)-N-(3-(5-amino-3-(fluoromethyl)-6,6-dimethyl-1,1-dioxido-3,6-dihydro-2H-1,4-thiazin-3-yl)-4-fluorophenyl)-5-(cyclobutylmethoxy)-3-methylpicolinamide

5-methoxy-3-methylpicolinic acid

Refernces

• 1、 O'Neill, Brian T.,Beck, Elizabeth M.,Butler, Christopher R.,Nolan, Charles E.,Gonzales, Cathleen,Zhang, Lei,Doran, Shawn D.,Lapham, Kimberly,Buzon, Leanne M.,Dutra, Jason K.,Barreiro, Gabriela,Hou, Xinjun,Martinez-Alsina, Luis A.,Rogers, Bruce N.,Villalobos, Anabella,Murray, John C.,Ogilvie, Kevin,Lachapelle, Erik A.,Chang, Cheng,Lanyon, Lorraine F.,Steppan, Claire M.,Robshaw, Ashley,Hales, Katherine,Boucher, Germaine G.,Pandher, Karamjeet,Houle, Christopher,Ambroise, Claude W.,Karanian, David,Riddell, David,Bales, Kelly R.,Brodney, Michael A.. "Design and Synthesis of Clinical Candidate PF-06751979: A Potent, Brain Penetrant, β-Site Amyloid Precursor Protein Cleaving Enzyme 1 (BACE1) Inhibitor Lacking Hypopigmentation". . p. 4476 - 4504. Retrieved 2018/05/31.
• 2、 -. "TETRAHYDROPYRANO[3,4-D][1,3]OXAZIN DERIVATIVES AND THEIR USE AS BACE INHIBITORS". . . Retrieved 2017/04/11.