2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Base Information

• Chemical Name: 2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
• CAS No.: 182230-43-9
• Molecular Formula: C16H14F3N5O
• Molecular Weight: 349.315
• Hs Code.: 2933997500
• European Community (EC) Number: 605-961-5
• ChEMBL ID: CHEMBL303329
• DSSTox Substance ID: DTXSID20411790
• Mol file: 182230-43-9.mol

Synonyms:182230-43-9;2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1,2,4-triazol-1-yl)butan-2-ol;rel-(R,S)-Voriconazole-d3;188416-29-7;(2R,3S/2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;(2RS,3RS)-alpha-(2,4-Difluorophenyl)-5-fluoro-beta-methyl-alpha-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethan;(2S,3R)-rel-2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;SCHEMBL824156;CHEMBL303329;DTXSID20411790;2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1h-1,2,4-triazol-1-yl)-2-butanol;BCEHBSKCWLPMDN-UHFFFAOYSA-N;BCP22611;AKOS015895147;NCGC00389311-01;4-pyrimidineethanol, alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1H-1,2,4-triazol-1-ylmethyl)-;A-(2,4-DIFLUOROPHENYL)-5-FLUORO-B-METHYL-A-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-4-PYRIMIDINEETHANOL;FT-0631154;FT-0658337;FT-0675848;FT-0675849;A24982;EN300-296133;2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol;(2R,3S/2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol;Rel-(2R, 3S)-Alpha-(2,4-Difluorophenyl)-5-fluoro-Beta-methyl-Alpha-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol

Chemical Property of 2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Chemical Property:

• Refractive Index: 1.617
• Boiling Point: 508.578 °C at 760 mmHg
• PKA: 11.54±0.29(Predicted)
• Flash Point: 261.379 °C
• PSA: 76.72000
• Density: 1.427 g/cm³
• LogP: 2.17690
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 349.11504457
• Heavy Atom Count: 25
• Complexity: 448

Purity/Quality:

99% ^*data from raw suppliers

Rel-(2R,3S)-α-(2,4-Difluorophenyl)-5-fluoro-β-methyl-α-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=NC=NC=C1F)C(CN2C=NC=N2)(C3=C(C=C(C=C3)F)F)O
• Uses: (2RS,3RS)α-(2,4-Difluorophenyl)-5-fluoro-β-methyl-α-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol (Voriconazole USP Related Compound A), is a derivative of Voriconazole (V760000), which is a triazole antifungal medication that is generally used to treat serious fungal infections.

Technology Process of 2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

There total 15 articles about 2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol 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: 92.5%

(2R,3S/2S,3R)-6-[4-(3,5-dibromo-1H-1,2,4-triazol-1-yl)-3-(2,4-difluorophenyl)-3-hydroxybutan-2-yl]-5-fluoropyrimidin-4-yl methanesulfonate → 2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (182230-43-9,137234-63-0,173967-54-9,188416-29-7)

Guidance literature:

With ammonium formate; palladium on carbon; In toluene; at 80 ℃; for 3h;

Reference yield: 85.0%

3-(6-chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (188416-35-5) → 2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (182230-43-9,137234-63-0,173967-54-9,188416-29-7)

Guidance literature:

With 5% Pd/C; hydrogen; sodium acetate; In methanol; at 25 - 30 ℃; for 0.0833333h; under 1500.15 - 3000.3 Torr;

Reference yield: 76.0%

3-(4-chloro-5-fluoropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol hydrochloride salt (188416-20-8) → 2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (182230-43-9,137234-63-0,173967-54-9,188416-29-7)

Guidance literature:

3-(4-chloro-5-fluoropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol hydrochloride salt; With palladium 10% on activated carbon; hydrogen; sodium acetate; In methanol; at 35 - 45 ℃; under 1500.15 - 3000.3 Torr; Large scale;

With sodium hydroxide; In water; at 0 - 10 ℃; for 1h; Inert atmosphere; Large scale;

upstream raw materials:

3-(6-chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol

1-(5-fluoropyrimidin-4-yl)ethyl-4-methyl benzenesulfonate

1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone

C₆H₅FN₂O

Downstream raw materials:

voriconazole

(2S,3R)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

2-(2,4difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)-butan-2-ol-R(-)-10-camphor sulphonate

1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone

Refernces

• 1、 -. "Voriconazole synthesis method". Paragraph 0011; 0048-0063. . Retrieved 2020/08/02.
• 2、 -. "Synthetic method of voriconazole intermediate". Paragraph 0059; 0060. . Retrieved 2016/10/20.