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6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one
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Name

6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one

 EINECS 256-139-4
CAS No. 43200-81-3 Density 1.653 g/cm3
PSA 79.21000 LogP 1.24130
Solubility N/A Melting Point 240.5-241.5 °C
Formula C11H7ClN4O2 Boiling Point 525.2 °C at 760 mmHg
Molecular Weight 262.655 Flash Point 271.5 °C
Transport Information N/A Appearance Yellow crystalline powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 43200-81-3 (6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one) Hazard Symbols N/A
Synonyms

6-(5-Chloropyrid-2-yl)-5-hydroxy-7-oxo-5,6-dihydropyrrolo[3,4-b]pyrazine;RP29307;5H-Pyrrolo[3,4-b]pyrazin-5-one,6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-hydroxy-;

Article Data 13

6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one Synthetic route

6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3.4-b]pyrazin-5-yl acetate

43200-81-3

6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions
ConditionsYield
With sulfuric acid In ethanol for 3h; Reflux;88.7%
43200-82-4

6-(5-chloro-2-pyridyl)-5,7-dioxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazine

43200-81-3

6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions
ConditionsYield
Stage #1: 6-(5-chloro-2-pyridyl)-5,7-dioxo-6,7-dihydro-5H-pyrrolo(3,4-b)pyrazine With potassium borohydride In 1,4-dioxane at 10 - 15℃; for 0.5h;
Stage #2: With water In 1,4-dioxane for 6h;		87.4%
With potassium borohydride; water In tetrahydrofuran at -10 - 5℃; for 3h; Large scale;70%
With potassium borohydride; potassium carbonate In 1,4-dioxane; water; N,N-dimethyl-formamide at 13℃; pH=11; Reagent/catalyst; Solvent; pH-value;95.5 g
With sodium hydroxide; sodium tetrahydroborate In water at 0 - 5℃; for 4 - 5h; Product distribution / selectivity;
138680-08-7

(-)-Zopiclone

43200-81-3

6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions
ConditionsYield
Stage #1: (-)-Zopiclone With trifluoroacetic acid In dichloromethane for 18h; Heating / reflux;
Stage #2: With water; sodium hydrogencarbonate In dichloromethane at 0℃; pH=7.5 - 8; Product distribution / selectivity;		70%
Stage #1: (-)-Zopiclone With trifluoroacetic acid In dichloromethane for 18h; Heating / reflux;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water at 0℃; pH=7.5 - 8; Product distribution / selectivity;		70%
Stage #1: (-)-Zopiclone With hydrogenchloride; water In methanol at 41℃; for 11h;
Stage #2: With sodium hydrogencarbonate In methanol; water at 10 - 15℃; Product distribution / selectivity;		41.24%
Stage #1: (-)-Zopiclone With hydrogenchloride; water In methanol at 41℃; for 11h;
Stage #2: With sodium hydrogencarbonate In methanol; water at 10 - 15℃; Product distribution / selectivity;		41.24%
With hydrogenchloride; water at 70℃; for 3h;
508169-18-4

(+/-)-7-(2-chloromethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

A

43200-81-3

6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

B

508169-20-8

(S)-(+)-7-(2-chloromethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions
ConditionsYield
With phosphate buffer; Candida antarctica lipase B Chirazyme-L2; triethylamine In water; toluene at 60℃; for 96h; pH=7;
508169-17-3

(+/-)-7-(2-chloroethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

A

43200-81-3

6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

B

508169-19-5

(S)-(+)-7-(2-chloroethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions
ConditionsYield
With phosphate buffer; Candida antarctica lipase B Novozym 435 In water; toluene at 60℃; for 96h; pH=7;
144025-94-5

(R)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate D-(+)-O,O'-dibenzoyltartaric acid salt

43200-81-3

6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions
ConditionsYield
Stage #1: (R)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate D-(+)-O,O'-dibenzoyltartaric acid salt With water; sodium hydrogencarbonate In dichloromethane; acetonitrile at 25 - 30℃; for 0.75h;
Stage #2: With hydrogenchloride; formic acid; water at 0 - 68℃; for 4h; Product distribution / selectivity;
508169-18-4

(+/-)-7-(2-chloromethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

A

1151528-25-4

(R)-5-(chloromethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-7-oxo-5,6-dihydropyrrolo[3,4-b]pyrazine

B

43200-81-3

6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

C

508169-20-8

(S)-(+)-7-(2-chloromethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions
ConditionsYield
With propan-1-ol; triethylamine; Novozyme 435 In toluene at 45℃; for 16 - 24h; Purification / work up; Enzymatic reaction; Resolution of racemate;A n/a
B n/a
C n/a
4744-50-7

2,3-pyrazinedicarboxylic anhydride

43200-81-3

6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dmap; triethylamine / 5,5-dimethyl-1,3-cyclohexadiene / 13 h / 0 °C / Reflux
2.1: potassium borohydride / 1,4-dioxane / 0.5 h / 10 - 15 °C
2.2: 6 h
View Scheme
Multi-step reaction with 3 steps
1.1: toluene / 2.5 h / 20 - 52 °C
1.2: 1 h / 10 - 15 °C
2.1: dichloromethane / 1 h / Heating / reflux
2.2: 0.75 - 1 h / 25 - 30 °C / Heating / reflux
3.1: sodium hydroxide; sodium tetrahydroborate / water / 4 - 5 h / 0 - 5 °C
View Scheme
Multi-step reaction with 2 steps
1: propionic acid anhydride / 1 h / 60 - 105 °C
2: potassium borohydride; water / tetrahydrofuran / 3 h / -10 - 5 °C / Large scale
View Scheme
1072-98-6

5-chloro-2-pyridylamine

43200-81-3

6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dmap; triethylamine / 5,5-dimethyl-1,3-cyclohexadiene / 13 h / 0 °C / Reflux
2.1: potassium borohydride / 1,4-dioxane / 0.5 h / 10 - 15 °C
2.2: 6 h
View Scheme
Multi-step reaction with 3 steps
1.1: toluene / 2.5 h / 20 - 52 °C
1.2: 1 h / 10 - 15 °C
2.1: dichloromethane / 1 h / Heating / reflux
2.2: 0.75 - 1 h / 25 - 30 °C / Heating / reflux
3.1: sodium hydroxide; sodium tetrahydroborate / water / 4 - 5 h / 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1: isopropyl alcohol / 5 h / Reflux; Large scale
2: 1 h / Reflux; Large scale
3: sulfuric acid / ethanol / 3 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: propionic acid anhydride / 1 h / 60 - 105 °C
2: potassium borohydride; water / tetrahydrofuran / 3 h / -10 - 5 °C / Large scale
View Scheme
43200-80-2

zopiclon

43200-81-3

6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: water; acetonitrile / 3 - 4.5 h / 25 - 80 °C / Resolution of racemate
2.1: water; sodium hydrogencarbonate / dichloromethane; acetonitrile / 0.75 h / 25 - 30 °C
2.2: 4 h / 0 - 68 °C
View Scheme

6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one Chemical Properties

IUPAC Name: 6-(5-Chloropyridin-2-yl)pyrrolo[3,4-b]pyrazine-5,7-dione
Synonyms of 6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one (CAS NO.43200-81-3): 5H-Pyrrolo[3,4-b]pyrazin-5-one,6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-hydroxy-
CAS NO: 43200-81-3
Molecular Formula: C11H7ClN4O2
Molecular Weight: 262.65
Molecular Structure:
EINECS: 256-139-4
H bond acceptors: 6
H bond donors: 1
Freely Rotating Bonds: 2
Polar Surface Area: 68.21 Å2
Index of Refraction: 1.719
Molar Refractivity: 62.71 cm3
Molar Volume: 158.8 cm3
Surface Tension: 95.4 dyne/cm
Density: 1.653 g/cm3
Flash Point: 271.5 °C
Enthalpy of Vaporization: 84.14 kJ/mol
Boiling Point: 525.2 °C at 760 mmHg
Vapour Pressure: 7.35E-12 mmHg at 25 °C
Appearance: Yellow Crystalline Powder
SMILES: Clc1ccc(nc1)N3C(=O)c2nccnc2C3O
InChI: InChI=1/C11H7ClN4O2/c12-6-1-2-7(15-5-6)16-10(17)8-9(11(16)18)14-4-3-13-8/h1-5,10,17H
InChIKey: FUUXOEKDNNWZTR-UHFFFAOYAP
Std. InChI: InChI=1S/C11H7ClN4O2/c12-6-1-2-7(15-5-6)16-10(17)8-9(11(16)18)14-4-3-13-8/h1-5,10,17H
Std. InChIKey: FUUXOEKDNNWZTR-UHFFFAOYSA-N
Product Categories of 6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one (CAS NO.43200-81-3): Aromatics Compounds; Aromatics; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals

6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one Uses

 6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one (CAS NO.43200-81-3) is used as Eszopiclone intermediate.

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