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Basic Information
CAS No.: 188416-35-5
Name: (2R,3S/2S,3R)-3-(4-Chloro-5-fluoro-6-pyrimidinyl)-2-(2,4-difluorophenyl)butan-2-ol hydrochloride
Molecular Structure:
Molecular Structure of 188416-35-5 ((2R,3S/2S,3R)-3-(4-Chloro-5-fluoro-6-pyrimidinyl)-2-(2,4-difluorophenyl)butan-2-ol hydrochloride)
Formula: C16H14Cl2F3N5O
Molecular Weight: 383.76
Synonyms: 3-(6-Chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)butan-2-ol;3-(6-chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)butan-2-ol,hydrochloride;
EINECS: 606-140-4
Density: 1.51
Melting Point: 183-187°C
Boiling Point: 550.9oC at 760 mmHg
Flash Point: 287oC
PSA: 76.72000
LogP: 2.83030
Related products
Synthetic route
188416-28-6

1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

86404-63-9

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

188416-35-5

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

Conditions
ConditionsYield
With lead; samarium diiodide; 1-benzyl-3-(2-pyridylmethyl)-1H-benzimidazolium chloride; iodine; zinc In tetrahydrofuran at -5 - 40℃; for 1.33333h; Inert atmosphere;87%
With zinc(II) chloride Reformatsky Reaction;
With hydrogenchloride; zinc In tetrahydrofuran; water
86404-63-9

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

137234-74-3

4-chloro-5-fluoro-6-ethylpyrimidine

188416-35-5

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

Conditions
ConditionsYield
Stage #1: 4-chloro-6-ethyl-5-fluoropyrimidine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane; n-heptane at -73 - 18℃; for 2.25h;
Stage #2: 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone In tetrahydrofuran; hexane; n-heptane at -74 - 55℃; for 5h;		26.3%
Stage #1: 4-chloro-6-ethyl-5-fluoropyrimidine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane; n-heptane at -80 - -70℃; for 0.25h; Inert atmosphere;
Stage #2: 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone In tetrahydrofuran; hexane; n-heptane at -80 - -55℃; for 2h; Inert atmosphere;
Stage #1: 4-chloro-6-ethyl-5-fluoropyrimidine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane; n-heptane at -80 - -70℃; for 0.25h; Inert atmosphere;
Stage #2: 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone In tetrahydrofuran; hexane; n-heptane at -80 - -55℃; for 2h;
Stage #3: With acetic acid In tetrahydrofuran; hexane; n-heptane; water at -70 - -10℃;
86404-63-9

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

188416-35-5

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

Conditions
ConditionsYield
With diisopropylamine In tetrahydrofuran; water; acetic acid

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

137234-74-3

4-chloro-5-fluoro-6-ethylpyrimidine

188416-35-5

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

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; n-heptane at -70 - -65℃; for 3 - 4h; pH=5 - 8;
137234-87-8

6-ethyl-5-fluoro-4-hydroxypyrimidine

188416-35-5

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / dichloromethane / 5 - 10 °C
1.2: 8 h / 10 - 55 °C / Reflux
1.3: 0.5 h / 15 - 20 °C
2.1: diisopropylamine; n-butyllithium / n-heptane; hexane; tetrahydrofuran / 0.25 h / -80 - -70 °C / Inert atmosphere
2.2: 2 h / -80 - -55 °C
2.3: -70 - -10 °C
View Scheme
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

188416-35-5

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

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water at 10℃; for 2h; pH=11;25 g
137234-74-3

4-chloro-5-fluoro-6-ethylpyrimidine

188416-35-5

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / dichloromethane / 16 h / 55 °C
2: hydrogenchloride; zinc / tetrahydrofuran; water
View Scheme
188416-35-5

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

A

86404-63-9

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

B

137234-74-3

4-chloro-5-fluoro-6-ethylpyrimidine

Conditions
ConditionsYield
With hydrogenchloride In water at 60 - 70℃; Temperature; Reagent/catalyst; Solvent;A 88.4%
B n/a
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
ConditionsYield
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%
188416-35-5

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

137234-62-9

voriconazole

Conditions
ConditionsYield
Stage #1: 3-(6-chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol With 5%-palladium/activated carbon; hydrogen; sodium acetate In methanol at 25℃; under 760.051 Torr;
Stage #2: With [(1R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid In methanol; acetone for 2h; Reflux;		35%
Multi-step reaction with 3 steps
1.1: sodium acetate / ethyl acetate; water / 0.5 h / 25 - 30 °C
1.2: 25 - 30 °C / 3677.86 Torr
1.3: 0.5 h / 20 - 25 °C
2.1: acetone; methanol / 15 h / -20 - 25 °C
3.1: sodium hydroxide / dichloromethane; water / 0.25 h / pH 11 - 14
View Scheme
Multi-step reaction with 4 steps
1.1: hydrogen; sodium acetate / palladium 10% on activated carbon / ethyl acetate; water / 25 - 30 °C / 3677.86 Torr
1.2: 0.5 h / 20 - 25 °C
1.3: 12.5 h / 25 - 30 °C
2.1: sodium hydroxide / dichloromethane; water / 0.5 h / pH 9 - 12
3.1: acetone; methanol / 15 h / -20 - 25 °C
4.1: sodium hydroxide / dichloromethane; water / 0.25 h / pH 11 - 14
View Scheme
Multi-step reaction with 4 steps
1.1: hydrogen; sodium acetate; sodium carbonate / palladium 10% on activated carbon / ethyl acetate; water / 25 - 30 °C / 3677.86 Torr
1.2: 0.5 h / 20 - 25 °C
1.3: 10 - 25 °C
2.1: potassium carbonate / dichloromethane; water / 0.5 h / pH 8 - 10
3.1: acetone; methanol / 15 h / -20 - 25 °C
4.1: sodium hydroxide / dichloromethane; water / 0.25 h / pH 11 - 14
View Scheme
Raw Materials
137234-74-3
137234-87-8
86404-63-9
Downstream Products
182230-43-9
137234-62-9
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    (2R,3S/2S,3R)-3-(4-Chloro-5-fluoro-6-pyrimidinyl)-2-(2,4-difluorophenyl)butan-2-ol hydrochloride

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Chemistry


Systematic Name: (2S,3R)-3-(6-chloro-5-fluoro-pyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1,2,4-triazol-1-yl)butan-2-ol hydrochloride
Molecular Formula: C16H13ClF3N5O.HCl
Molecular Weight: 420.22 g/mol
Canonical SMILES: CC(c1c(c(ncn1)Cl)F)C(Cn2cncn2)(c3ccc(cc3F)F)O.Cl
InChI: InChI=1/C16H13ClF3N5O.ClH/c1-9(14-13(20)15(17)23-7-22-14)16(26,5-25-8-21-6-24-25)11-3-2-10(18)4-12(11)19;/h2-4,6-9,26H,5H2,1H3;1H/t9-,16+;/m1./s1
Product Categories: Intermediatesofvoriconazole
H bond acceptors: 6
H bond donors: 1
Freely Rotating Bonds: 6
Polar Surface Area: 76.72
Flash Point: 287 °C
Enthalpy of Vaporization: 87.46 kJ/mol
Boiling Point: 550.9 °C at 760 mmHg
Vapour Pressure of (2R,3S/2S,3R)-3-(4-Chloro-5-fluoro-6-pyrimidinyl)-2-(2,4-difluorophenyl)butan-2-ol hydrochloride (CAS NO.188416-35-5): 5.69E-13 mmHg at 25 °C

Specification

 (2R,3S/2S,3R)-3-(4-Chloro-5-fluoro-6-pyrimidinyl)-2-(2,4-difluorophenyl)butan-2-ol hydrochloride (CAS NO.188416-35-5), its Synonyms are (2R,3S/2S,3R)-3-(4-Chloro-5-fluoro-6-pyrimidinyl)-2-(2,4-difluorophenyl)-1- (1H- ; (2R,3S/2S,3R)-3-(4-Chloro-5-fluoro-6-pyrimidinyl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol- 1-yl)-2- butanol hydrochloride ; (2R,3S/2S,3R)-3-(6-Chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol- 1-yl)-2- butanol hydrochloride .