3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one supplier

Name
3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one
EINECS 603-382-2
CAS No. 130049-82-0
Article Data25
CAS DataBase
Density 1.41 g/cm³
Solubility
Melting Point 100-102°C
Formula C₁₁H₁₅O₂N₂Cl
Boiling Point 389.3 °C at 760 mmHg
Molecular Weight 242.705
Flash Point 189.2 °C
Transport Information
Appearance pale-yellow solid
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one;3-(2-Chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one;3-(2-Chloroethyl)-9-hydroxy-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one;9-Hydroxy-3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one;
PSA 55.12000
LogP 1.16020

Synthetic route

: 260273-82-3
3-(2-chloroethyl)-2-methyl-9-hydroxy-4H-pyrido[1,2-a]pyrimidin-4-one

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
Stage #1: 3-(2-chloroethyl)-2-methyl-9-hydroxy-4H-pyrido[1,2-a]pyrimidin-4-one With hydrogenchloride; palladium 10% on activated carbon In ethanol; water Green chemistry; Stage #2: With hydrogen In ethanol; water at 80℃; under 11251.1 Torr; Catalytic behavior; Solvent; Reagent/catalyst; Temperature; Pressure; Green chemistry;	99.32%
Stage #1: 3-(2-chloroethyl)-2-methyl-9-hydroxy-4H-pyrido[1,2-a]pyrimidin-4-one With hydrogen; palladium 10% on activated carbon In acetic acid at 25 - 30℃; under 2206.72 Torr; Stage #2: With sodium hydroxide In dichloromethane; water pH=5.5 - 6.0; Product distribution / selectivity;
With hydrogen; palladium 10% on activated carbon In acetic acid at 35℃; under 735.572 - 2206.72 Torr; Product distribution / selectivity;

: 849727-62-4
3-(2-chloroethyl)-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
Stage #1: 3-(2-chloroethyl)-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride With hydrogen; 5%-palladium/activated carbon In water; isopropyl alcohol at 55℃; under 760.051 Torr; Inert atmosphere; Stage #2: With potassium acetate In water Product distribution / selectivity;	92%
Stage #1: 3-(2-chloroethyl)-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride In methanol at 50 - 55℃; Stage #2: With hydrogen; palladium 10% on activated carbon In methanol at 50 - 55℃; for 8h;	68.25%
Stage #1: 3-(2-chloroethyl)-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride With pyrographite In methanol at 50 - 55℃; for 0.75h; Large scale; Stage #2: With palladium 10% on activated carbon; hydrogen In methanol; dichloromethane at 25 - 30℃; under 2172.08 - 2947.82 Torr; Large scale;	39%

: 1204248-71-4
C11H14ClN3O2

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
Stage #1: C11H14ClN3O2 With hydrogenchloride; titanium(III) chloride; water at 70℃; for 0.5h; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In water	87%

: 147687-17-0
9-(benzyloxy)-3-(2-chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In methanol; water; tert-butyl alcohol at 25 - 30℃; under 775.743 Torr; for 16h; Reagent/catalyst; Solvent; Pressure;	74.4%
With hydrogenchloride; hydrogen; palladium 10% on activated carbon In water at 25 - 30℃;	69%
With cyclohexene; palladium 10% on activated carbon for 19h; Product distribution / selectivity; Heating / reflux;

: 130049-79-5
9-benzyloxy-3-(2-chloro-ethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
Stage #1: 9-benzyloxy-3-(2-chloro-ethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one With hydrogenchloride; hydrogen; 5% palladium over charcoal In methanol at 27℃; for 36h; pH=3.0; Inert atmosphere; Stage #2: With sodium hydroxide In water at 5℃; pH=10 - 11;	72.6%
With hydrogenchloride; hydrogen; palladium 10% on activated carbon In water at 25 - 30℃; under 735.572 - 1471.14 Torr; for 4 - 6h;	69%

: 1117803-76-5
3-(2-chloroethyl)-6,7,8,9-tetrahydro-9-acetyloxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With sodium hydroxide In water

: 1254173-48-2
3-(2-chloroethyl)-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
Stage #1: 3-(2-chloroethyl)-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride With hydrogen; 1% Pd/C In acetic acid at 35℃; under 2206.72 - 2574.5 Torr; for 6h; Stage #2: With sodium hydroxide In water at 0℃; for 1h; pH=6; Product distribution / selectivity;

: 147687-17-0
9-(benzyloxy)-3-(2-chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

A: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

B: 260273-82-3
3-(2-chloroethyl)-2-methyl-9-hydroxy-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; 1% Pd/C In methanol; water at 25 - 30℃; under 735.572 - 1471.14 Torr; for 1h; Product distribution / selectivity; Autoclave;	A 28.8 %Chromat. B 62 %Chromat.

: 147687-17-0
9-(benzyloxy)-3-(2-chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

A: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

B: 849903-79-3
3-ethyl-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; 1% Pd/C In methanol; water at 25 - 30℃; under 735.572 - 1471.14 Torr; for 3.5h; Product distribution / selectivity; Autoclave;	A 48.9 %Chromat. B 39 %Chromat.

: 1228559-69-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one oxalate

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With potassium acetate In water at 0 - 5℃; for 1h; pH=4.8;

: 517-23-7
3-acetyl-2-oxo-4,5-dihydrofuran

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / xylene / 20.5 h / 25 - 142 °C 2: hydrogenchloride / isopropyl alcohol; methanol / 1 h / 60 - 65 °C / pH 1 - 3 3: hydrogen; zinc(II) chloride / palladium on carbon / methanol / 35 - 55 °C View Scheme
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / xylene / Reflux 2: thionyl chloride / N,N-dimethyl-formamide / 65 - 70 °C 3: hydrogen / palladium 10% on activated carbon / methanol / 23 - 30 °C / 1471.14 - 2206.72 Torr View Scheme
Multi-step reaction with 2 steps 1.1: trichlorophosphate / toluene 1.2: 7 h / 90 - 95 °C 1.3: 1 h / 90 - 95 °C 2.1: hydrogen / palladium 10% on activated carbon / acetic acid / 35 °C / 735.57 - 2206.72 Torr View Scheme
Multi-step reaction with 3 steps 1.1: toluene / 0.25 h 1.2: 20 h / 70 °C / Reflux 2.1: hydrogenchloride / toluene; water / 9 h / 65 - 70 °C 3.1: hydrogen; palladium on activated charcoal; acetic acid / 6 h / 35 °C / 2250.23 - 2625.26 Torr / Autoclave View Scheme
Multi-step reaction with 2 steps 1.1: trichlorophosphate / toluene / 24 h / 30 - 40 °C / Large scale 1.2: 0 - 5 °C / Large scale 2.1: pyrographite / methanol / 0.75 h / 50 - 55 °C / Large scale 2.2: 25 - 30 °C / 2172.08 - 2947.82 Torr / Large scale View Scheme

: 181525-38-2
9-hydroxy-3-hydroxyethyl-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / isopropyl alcohol; methanol / 1 h / 60 - 65 °C / pH 1 - 3 2: hydrogen; zinc(II) chloride / palladium on carbon / methanol / 35 - 55 °C View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / N,N-dimethyl-formamide / 65 - 70 °C 2: hydrogen / palladium 10% on activated carbon / methanol / 23 - 30 °C / 1471.14 - 2206.72 Torr View Scheme

: 16867-03-1
2-amino-3-hydroxypyridine

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / xylene / 20.5 h / 25 - 142 °C 2: hydrogenchloride / isopropyl alcohol; methanol / 1 h / 60 - 65 °C / pH 1 - 3 3: hydrogen; zinc(II) chloride / palladium on carbon / methanol / 35 - 55 °C View Scheme
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / xylene / Reflux 2: thionyl chloride / N,N-dimethyl-formamide / 65 - 70 °C 3: hydrogen / palladium 10% on activated carbon / methanol / 23 - 30 °C / 1471.14 - 2206.72 Torr View Scheme
Multi-step reaction with 2 steps 1.1: trichlorophosphate / toluene / 24 h / 30 - 40 °C / Large scale 1.2: 0 - 5 °C / Large scale 2.1: pyrographite / methanol / 0.75 h / 50 - 55 °C / Large scale 2.2: 25 - 30 °C / 2172.08 - 2947.82 Torr / Large scale View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide; tetrabutylammomium bromide / water / 6 h / 40 - 75 °C / Large scale 2: toluene-4-sulfonic acid / toluene / Reflux; Large scale 3: trichlorophosphate / 1,2-dimethoxyethane / 6 h / Reflux; Large scale 4: hydrogenchloride; palladium 10% on activated carbon; hydrogen / water; methanol; tert-butyl alcohol / 16 h / 25 - 30 °C / 775.74 Torr View Scheme

: 517-23-7
3-acetyl-2-oxo-4,5-dihydrofuran

: 24016-03-3
2-amino-3-benzyloxypyridine

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; trichlorophosphate In cyclohexane; acetic acid; toluene

: 24016-03-3
2-amino-3-benzyloxypyridine

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trichlorophosphate / toluene 1.2: 7 h / 90 - 95 °C 1.3: 1 h / 90 - 95 °C 2.1: hydrogen / palladium 10% on activated carbon / acetic acid / 35 °C / 735.57 - 2206.72 Torr View Scheme
Multi-step reaction with 3 steps 1.1: toluene / 0.25 h 1.2: 20 h / 70 °C / Reflux 2.1: hydrogenchloride / toluene; water / 9 h / 65 - 70 °C 3.1: hydrogen; palladium on activated charcoal; acetic acid / 6 h / 35 °C / 2250.23 - 2625.26 Torr / Autoclave View Scheme
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / toluene / Reflux; Large scale 2: trichlorophosphate / 1,2-dimethoxyethane / 6 h / Reflux; Large scale 3: hydrogenchloride; palladium 10% on activated carbon; hydrogen / water; methanol; tert-butyl alcohol / 16 h / 25 - 30 °C / 775.74 Torr View Scheme

: 3-(2-chloroethyl)-9-hydroxy-2-methyl-4H-pyrido-[1,2-a]pyrimidin-4-one hydrochloride

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen; acetic acid at 35℃; under 2250.23 - 2625.26 Torr; for 6h; Time; Temperature; Autoclave;	22 g

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: 138271-16-6
(Z)-(2,4-difluorophenyl) (4-piperidinyl)methanone, oxime monohydrochloride

: C23H28F2N4O3

Conditions

Conditions	Yield
With potassium iodide; sodium hydroxide In acetonitrile for 10h; Reflux;	99.2%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: 107-30-2
chloromethyl methyl ether

: 3-(2-chloroethyl)-9-(methoxymethoxy)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-α]pyrimidin-4-one

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 45℃; Reagent/catalyst;	98%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: 57-10-3
1-hexadecylcarboxylic acid

: 1415488-05-9
3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-9-hydroxy-4H-pyrido[1,2-a]pyrimidine-4-one palmitate ester

Conditions

Conditions	Yield
Stage #1: 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one; 1-hexadecylcarboxylic acid With dmap; triethylamine In dichloromethane at 25 - 30℃; for 0.25h; Stage #2: With pivaloyl chloride In dichloromethane at 25 - 40℃; for 2h;	95%
Stage #1: 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one; 1-hexadecylcarboxylic acid With dmap; triethylamine In dichloromethane at 25 - 30℃; for 0.25h; Stage #2: With pivaloyl chloride In dichloromethane at 25 - 40℃; for 2h;	95%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: 84163-13-3
6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride

: 144598-75-4
paliperidone

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In methanol for 24h; Reflux;	94%
With N-ethyl-N,N-diisopropylamine In methanol Product distribution / selectivity; Reflux;	93%
With N-ethyl-N,N-diisopropylamine In methanol at 60℃; Reagent/catalyst; Inert atmosphere;	90%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: 124-63-0
methanesulfonyl chloride

: C12H17ClN2O4S

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.5h; Cooling with ice;	93%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: 3-(1-chloropiperidin-4-yl)-6-fluoro benzisoxazole

: 144598-75-4
paliperidone

Conditions

Conditions	Yield
With diisopropylamine In methanol for 12h; Time; Inert atmosphere; Reflux;	88%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: C18H19NOS*C2H2O4

: 9-hydroxy-2-methyl-3-(2-(methyl((S)-3-(naphthalen-1-yloxy)-3-(thiophen-3-yl)propyl)amino)ethyl)-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In tetrahydrofuran Reflux;	82%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: 3-(2-chloroethyl)-9-fluoro-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With diethylamino-sulfur trifluoride In dichloromethane at 20℃; for 3h; Cooling with ice;	74%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: 136434-34-9
duloxetine hydrochloride

: 9-hydroxy-2-methyl-3-(2-(methyl((S)-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propyl)amino)ethyl)-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 65℃; Inert atmosphere;	72%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: 135634-18-3
(2,4-difluorophenyl)-piperidin-4-yl-methanone oxime hydrochloride

: 1141761-80-9
3-(2-{4-((2,4-difluorophenyl)hydroxyiminomethyl)piperidin-1-yl}ethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 16h; Reflux;	70%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: 84163-77-9
6-fluoro-3-(4-piperidinyl)benzo[d]isoxazole

: 144598-75-4
paliperidone

Conditions

Conditions	Yield
With sodium hydrogencarbonate; potassium iodide In water; acetonitrile at 65℃; for 16h; Reagent/catalyst; Solvent; Temperature;	60%
With N-ethyl-N,N-diisopropylamine In methanol at 50 - 70℃;	55%
With sodium carbonate In ethanol at 58 - 62℃; for 24h; Product distribution / selectivity;

: 1-(benzo[b]thiophen-4-yl)piperazine hydrochloride

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: 3-(2-(4-(benzo[b]thiophen-4-yl)piperazin-1-yl)ethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 85℃;	58%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: 1-(2,3-dihydrobenzo[b]thiophen-4-yl)piperazine hydrochloride

: 3-(2-(4-(2,3-dihydrobenzo[b]thiophen-4-yl)piperazin-1-yl)ethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 85℃;	56%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: 4-(benzo[b]thiophen-4-yl)piperidine trifluoroacetate

: 3-(2-(4-(benzo[b]thiophen-4-yl)piperidin-1-yl)ethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 12h; Reflux;	49%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: C27H31F2N5O4

: 3-(2-(4-(4-fluoro-2-(4-(6-fluorobenzo[d]isooxazol-3-yl)piperazin-1-yl)benzoyl)piperazine-1-yl)ethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
Stage #1: C27H31F2N5O4 In ethanol at 20 - 30℃; Acidic conditions; Stage #2: 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one With N-ethyl-N,N-diisopropylamine In methanol Reflux;	49%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: 4-(piperazin-1-yl)thieno[2,3-c]pyridine trifluoroacetate

: 9-hydroxy-2-methyl-3-(2-(4-(thieno[2,3-c]pyridin-4-yl)piperazin-1-yl)ethyl)-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 80℃;	46.6%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: 849727-63-5
(±)-3-(2-chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water; butanone pH=2;	46%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: C28H32F2N4O4

: 3-(2-(4-(4-fluoro-2-(4-(6-fluorobenzo[d]isooxazol-3-yl)piperazin-1-yl)benzoyl)piperidine-1-yl)ethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
Stage #1: C28H32F2N4O4 In ethanol at 20 - 30℃; Acidic conditions; Stage #2: 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one With N-ethyl-N,N-diisopropylamine In methanol Reflux;	42%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: 4-(piperazin-1-yl)thieno[2,3-d]pyrimidine trifluoroacetate

: 9-hydroxy-2-methyl-3-(2-(4-(thieno[2,3-d]pyrimidin-4-yl)piperazin-1-yl)ethyl)-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile Reflux;	41%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: C28H32F2N4O4

: 3-(2-(4-(4-fluoro-2-(4-(6-fluorobenzo[d]isooxazol-3-yl)piperidin-1-yl)benzoyl)piperazine-1-yl)ethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
Stage #1: C28H32F2N4O4 In ethanol at 20 - 30℃; Acidic conditions; Stage #2: 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one With N-ethyl-N,N-diisopropylamine In methanol Reflux;	41%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: C24H25F2N3O2*ClH

: 3-(2-(4-(4-fluoro-2-(4-(6-fluorobenzo[d]isooxazol-3-yl)piperidin-1-yl)benzoyl)piperidine-1-yl)ethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In methanol Reflux;	36%

: 130049-82-0
3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

: C24H26F2N4O*ClH

: 3-(2-(4-(4-fluoro-2-(4-(6-fluoro-1H-indazol-3-yl)piperidin-1-yl)benzoyl)piperidin-1-yl)ethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In methanol Reflux;	36%

3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one Chemical Properties

Empirical Formula: C₁₁H₁₅ClN₂O₂
Molecular Weight: 242.702g/mol
Structure of 4H-Pyrido[1,2-a]pyrimidin-4-one,3-(2-chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl- (CAS NO.130049-82-0):

Index of Refraction: 1.634
Molar Refractivity: 61.26 cm³
Molar Volume: 171.1 cm³
Polarizability: 24.28×10^-24cm³
Surface Tension: 50.3 dyne/cm
Density: 1.41 g/cm³
Flash Point: 189.2 °C
Enthalpy of Vaporization: 73.84 kJ/mol
Boiling Point: 389.3 °C at 760 mmHg
Vapour Pressure: 1.14E-07 mmHg at 25°C
Product Categories: Heterocyclic Compounds;Bases & Related Reagents;Heterocycles;Nucleotides
Systematic Name: 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one
SMILES: O=C2C(/CCCl)=C(/C)\N=C1\C(O)CCCN12
InChI: InChI=1/C11H15ClN2O2/c1-7-8(4-5-12)11(16)14-6-2-3-9(15)10(14)13-7/h9,15H,2-6H2,1H3
InChIKey: JKVUGXRJSYRXFN-UHFFFAOYAK

3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one Specification

4H-Pyrido[1,2-a]pyrimidin-4-one,3-(2-chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl- , its cas register number is 130049-82-0. It also can be called 3-(2-Chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one . 4H-Pyrido[1,2-a]pyrimidin-4-one,3-(2-chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl- (CAS NO.130049-82-0) is a pale-yellow solid.

Product Name

3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Synthetic route

3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one Chemical Properties

3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one Specification

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