• Name

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

• EINECS 605-961-5
• CAS No. 182230-43-9
• Article Data9
• CAS DataBase
• Density 1.427 g/cm³
• Solubility
• Melting Point
• Formula C₁₆H1₄F₃N₅O
• Boiling Point 508.578 °C at 760 mmHg
• Molecular Weight 349.315
• Flash Point 261.379 °C
• Transport Information
• Appearance
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 4-Pyrimidineethanol, a-(2,4-difluorophenyl)-5-fluoro-b-methyl-a-(1H-1,2,4-triazol-1-ylmethyl)-;(2r,3s/2s,3r)-3-(5-Fluoro-6-Pyrimidinyl)-2-(2,4-Difluorophenyl)-1-(1h-1,2,4-Triazol- 1-Yl)-2- Butanol Hydrochloride;
• PSA 76.72000
• LogP 2.17690

Synthetic route

(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

182230-43-9

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

Conditions

Conditions	Yield
With ammonium formate; palladium on carbon In toluene at 80℃; for 3h;	92.5%

188416-35-5

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

182230-43-9

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

Conditions

Conditions	Yield
With 5% Pd/C; hydrogen; sodium acetate In methanol at 25 - 30℃; under 1500.15 - 3000.3 Torr; for 0.0833333h;	85%
With hydrogen; sodium acetate; Raney nickel In methanol at 54 - 56℃; under 2206.72 - 3677.86 Torr; for 5h;	66.4%

188416-20-8

3-(4-chloro-5-fluoropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol hydrochloride salt

182230-43-9

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

Conditions

Conditions	Yield
Stage #1: 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; Stage #2: With sodium hydroxide In water at 0 - 10℃; for 1h; Inert atmosphere; Large scale;	76%

1289559-67-6

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

86404-63-9

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

182230-43-9

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

Conditions

Conditions	Yield
With zinc(II) chloride; zinc In tetrahydrofuran at 0 - 30℃; Product distribution / selectivity;

1289559-75-6

C6H5FN2O

182230-43-9

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / ethanol / 5 h 2: triethylamine / dmap / dichloromethane / 20 - 30 °C 3: zinc; zinc(II) chloride / tetrahydrofuran / 0 - 30 °C View Scheme

1289559-65-4

1-(2,6-dichloro-5-fluoropyrimidin-4-yl)ethanone

182230-43-9

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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogen; sodium acetate / palladium on activated carbon / ethanol / 25 °C 2: sodium tetrahydroborate / ethanol / 5 h 3: triethylamine / dmap / dichloromethane / 20 - 30 °C 4: zinc; zinc(II) chloride / tetrahydrofuran / 0 - 30 °C View Scheme

1289559-66-5

1-(5-fluoropyrimidin-4-yl)ethanol

182230-43-9

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dmap / dichloromethane / 20 - 30 °C 2: zinc; zinc(II) chloride / tetrahydrofuran / 0 - 30 °C View Scheme

51336-94-8

2-chloro-1-(2,4-dichlorophenyl)ethanone

182230-43-9

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / tetrahydrofuran / 7 h / 20 °C 2: lead; zinc; iodine / tetrahydrofuran / -15 - 20 °C / Inert atmosphere 3: ammonium formate / palladium on carbon / toluene / 3 h / 80 °C View Scheme

137234-87-8

6-ethyl-5-fluoro-4-hydroxypyrimidine

182230-43-9

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

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 5 h / 20 °C 2: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / dichloromethane / 12 h / 45 - 50 °C 3: lead; zinc; iodine / tetrahydrofuran / -15 - 20 °C / Inert atmosphere 4: ammonium formate / palladium on carbon / toluene / 3 h / 80 °C View Scheme

1237496-99-9

6-ethyl-5-fluoropyrimidin-4-yl methanesulfonate

182230-43-9

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / dichloromethane / 12 h / 45 - 50 °C 2: lead; zinc; iodine / tetrahydrofuran / -15 - 20 °C / Inert atmosphere 3: ammonium formate / palladium on carbon / toluene / 3 h / 80 °C View Scheme

1237497-00-5

6-(1-bromoethyl)-5-fluoropyrimidin-4-yl methanesulfonate

182230-43-9

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lead; zinc; iodine / tetrahydrofuran / -15 - 20 °C / Inert atmosphere 2: ammonium formate / palladium on carbon / toluene / 3 h / 80 °C View Scheme

906451-64-7

1-(2,4-difluorophenyl)-2-(3,5-dibromo-1H-1,2,4-triazol-1-yl)ethanone

182230-43-9

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lead; zinc; iodine / tetrahydrofuran / -15 - 20 °C / Inert atmosphere 2: ammonium formate / palladium on carbon / toluene / 3 h / 80 °C View Scheme

137234-74-3

4-chloro-5-fluoro-6-ethylpyrimidine

182230-43-9

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / dichloromethane / 16 h / 55 °C 2: hydrogenchloride; zinc / tetrahydrofuran; water 3: 5%-palladium/activated carbon; methanol; potassium formate / 45 °C / Inert atmosphere View Scheme

35963-20-3

(R)-10-camphorsulfonic acid

182230-43-9

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

188416-34-4, 137234-71-0

(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonate

Conditions

Conditions	Yield
In methanol at 0 - 2℃; Product distribution / selectivity;	81.52%
In acetone at 45 - 55℃; for 2h; Large scale;	70%
In methanol; acetone for 1h; Reflux;	40%

35963-20-3

(R)-10-camphorsulfonic acid

182230-43-9

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

voriconazole L-camphorsulfate

Conditions

Conditions	Yield
In water; acetone at 20 - 50℃; for 2h; Temperature;	40.4%

3144-16-9

(1S)-10-camphorsulfonic acid

182230-43-9

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

321589-01-9

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

Conditions

Conditions	Yield
In methanol; acetone at 15 - 65℃; for 3.25h;

182230-43-9

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

137234-62-9

voriconazole

Conditions

Conditions	Yield
Stage #1: 2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol With (R)-10-camphorsulfonic acid In methanol; acetone at 25 - 60℃; for 2h; Stage #2: With sodium hydroxide In dichloromethane; water; isopropyl alcohol at 20 - 30℃; pH=12 - 13; Product distribution / selectivity;
With (1S)-10-camphorsulfonic acid In methanol; acetone at 20 - 30℃; for 3.5h; Reflux;
Multi-step reaction with 2 steps 1: sodium hydroxide / water / 3 h / 45 °C 2: camphor-10-sulfonic acid / methanol; acetone View Scheme

182230-43-9

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

A

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

B

137234-62-9

voriconazole

Conditions

Conditions	Yield
With 3-aminopropyl silica-supported chitosan bis(3,4-dichlorophenylcarbamate)(n-octylurea) In hexane; isopropyl alcohol Resolution of racemate;

182230-43-9

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

A

C6H7FN2

B

86404-63-9

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

Conditions

Conditions	Yield
With sodium hydroxide In water at 45℃; for 3h;

152-74-9

Rose-Bengale

182230-43-9

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

C20H4Cl4I4O5*C16H14F3N5O

Conditions

Conditions	Yield
In aq. buffer pH=2;

(2R,3S/2S,3R)-2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical Properties

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