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

Base Information

• Chemical Name: 3-(2-chloroethyl)-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one hydrochloride
• CAS No.: 849727-62-4
• Molecular Formula: C11H12Cl2N2O2
• Molecular Weight: 275.134
• Mol file: 849727-62-4.mol

Synonyms:Paliperidone Tetradehydro Chloroethyl Impurity;3-(2-chloroethyl)-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one hydrochloride

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

Chemical Property:

• Vapor Pressure: 0-0Pa at 20-25℃
• PSA: 54.60000
• Density: 1.6g/cm3 at 20℃
• LogP: 2.29180
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99.9% ^*data from raw suppliers

3-(2-Chloroethyl)-9-hydroxy-2-methyl-4H-Pyrido[1,2-a]pyrimidin-4-oneHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-(2-Chloroethyl)-9-hydroxy-2-methyl-4H-Pyrido[1,2-a]pyrimidin-4-one Hydrochloride is an intermediate in the synthesis of analog of Paliperidone (P141000), a combined serotonin and dopamine receptor antagonist.

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

There total 7 articles about 3-(2-chloroethyl)-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one hydrochloride 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: 82.82%

9-(benzyloxy)-3-(2-chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (147687-17-0) → 3-(2-chloroethyl)-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride (849727-62-4)

Guidance literature:

9-(benzyloxy)-3-(2-chloroethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one; With hydrogenchloride; In water; at 25 - 75 ℃; for 2.5h;

In water; acetone; at 5 - 30 ℃; for 1h;

Reference yield: 76.0%

2-amino-3-hydroxypyridine (16867-03-1) + 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7,594837-91-9,98634-97-0,313643-49-1) → 3-(2-chloroethyl)-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride (849727-62-4)

Guidance literature:

2-amino-3-hydroxypyridine; 3-acetyl-2-oxo-4,5-dihydrofuran; With trichlorophosphate; In toluene; at 30 - 40 ℃; for 24h; Large scale;

With hydrogenchloride; In isopropyl alcohol; at 0 - 5 ℃; Large scale;

DOI:10.1080/00304948.2016.1165060

Reference yield:

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

Guidance literature:

With thionyl chloride; In N,N-dimethyl-formamide; at 20 - 70 ℃;

upstream raw materials:

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

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

3-acetyl-2-oxo-4,5-dihydrofuran

2-amino-3-hydroxypyridine

Downstream raw materials:

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

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

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

(+)-Paliperidone

Refernces

• 1、 -. "PROCESS FOR PREPARATION OF PALIPERIDONE". Page/Page column 10. . Retrieved 2012/04/17.
• 2、 -. "NOVEL AND IMPROVED PROCESSES FOR THE PREPARATION OF PALIPERIDONE". . . Retrieved 2011/12/13.