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

Base Information

• Chemical Name: 3-(2-Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4h-pyrido[1,2-a]pyrimidin-4-one
• CAS No.: 63234-80-0
• Molecular Formula: C11H15ClN2O
• Molecular Weight: 226.706
• Hs Code.: 2933990090
• UNII: 2089CR1AQN
• DSSTox Substance ID: DTXSID00212626
• Nikkaji Number: J2.208.362G
• Wikidata: Q27253442
• Mol file: 63234-80-0.mol

Synonyms:63234-80-0;3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4h-pyrido[1,2-a]pyrimidin-4-one;3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4h-pyrido[1,2-a]pyrimidin-4-one;3-(2-Chloro-ethyl)-2-methyl-6,7,8,9-tetrahydro-pyrido[1,2-a]pyrimidin-4-one;3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4h-pyrido[1,2-a]-pyrimidin-4-one;Risperidone impurity L [EP];3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one;Piperidopyrimidinone intermediate;UNII-2089CR1AQN;3-(2-Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4hpyrido(1,2-a)pyrimidin-4-one;2089CR1AQN;3-(2-chloroethyl)-2-methyl-4H,6H,7H,8H,9H-pyrido[1,2-a]pyrimidin-4-one;MFCD06200813;3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido(1,2a)pyrimidine-4-one;4H-Pyrido(1,2-a)pyrimidin-4-one, 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-;3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-4-one;3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4h-pyrido[1,2-a]pyrimidine-4-one;3-(2-Chloroethyl-d4)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one;3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4h-pyrido(1,2-a)pyrimidin-4-one;3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4h-pyrido(1,2-a)pyrimidin-4-one;Risperidone EP Impurity L;SCHEMBL460865;DTXSID00212626;CMWCQQUYLPYOMY-UHFFFAOYSA-N;BCP11946;BBL010804;STK617737;AKOS005552077;AC-3457;CS-W014205;PB10329;SB10296;3-2(2-Chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-Pyrido[1,2-a]Pyrimdin-4-one;AS-73540;SY047063;A8722;C2433;FT-0640879;FT-0705669;RISPERIDONE IMPURITY L [EP IMPURITY];1,2-Benzisoxazole,4-fluoro-3-(4-piperidinyl)-;EN300-7388138;J-510497;Q27253442;3-(2-Chloroethyl)-6,7,8,9-TH-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one;3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4h-pyridino(1,2-a)-pyrimidine-4-one;3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4h-pyridino(1,2a)pyrimidine-4-one;3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4h-pyrido[1,2-a]-pyrimidin-4 one;3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4h-pyridino[1,2-a]pyrimidine-4-one;3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4h-pyrido [1,2-a] pyrimidin-4-one;3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4h-pyrido [1,2-a]pyrimidine-4-one;3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4h-pyrido 1,2-a pyrimidin-4-one;3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[ 1,2-a]pyrimidin-4-one;3-(2-chloroethyl)-6,7,8,9-tetrahydro-2methyl-4h-pyrido[1,2-a]pyrimidin-4-one;4H-Pyrido[1,2-a]pyrimidin-4-one,3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-;3-(2-Chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, AldrichCPR

Chemical Property of 3-(2-Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4h-pyrido[1,2-a]pyrimidin-4-one

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 0.000111mmHg at 25°C
• Melting Point: 68.5-69.5 °C
• Refractive Index: 1.611
• Boiling Point: 336.6 °C at 760 mmHg
• PKA: 3.58±0.70(Predicted)
• Flash Point: 157.4 °C
• PSA: 34.89000
• Density: 1.3 g/cm³
• LogP: 1.66930
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 226.0872908
• Heavy Atom Count: 15
• Complexity: 347

Purity/Quality:

99% ^*data from raw suppliers

3-(2-Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)N2CCCCC2=N1)CCCl
• Uses: 3-(2-Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (Risperidone EP Impurity L) is an intermediate in the synthesis of Risperidone (R525000), which is a combined serotonin (5-HT2) and dopamine (D2) receptor antagonist.

Technology Process of 3-(2-Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4h-pyrido[1,2-a]pyrimidin-4-one

There total 6 articles about 3-(2-Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4h-pyrido[1,2-a]pyrimidin-4-one 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: 90.0%

3-(2-chloro-ethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (41078-70-0) → 3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (63234-80-0)

Guidance literature:

With hydrogenchloride; hydrogen; palladium; In water; at 20 ℃; for 8h; under 1810.07 Torr;

Reference yield:

3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride (93076-03-0) → 3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (63234-80-0)

Guidance literature:

With sodium carbonate; potassium iodide; In water; 4-methyl-2-pentanone; Product distribution / selectivity;

Reference yield:

2-aminopyridine (504-29-0) → 3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one (63234-80-0)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / toluene / Reflux

2: trichlorophosphate / 1 h / Reflux

3: palladium 10% on activated carbon; hydrogen / methanol

With palladium 10% on activated carbon; hydrogen; toluene-4-sulfonic acid; trichlorophosphate; In methanol; toluene;

DOI:10.2174/157018011797655304

upstream raw materials:

3-(2-chloro-ethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

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

2-aminopyridine

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

Downstream raw materials:

Risperidone

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

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

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

Refernces

• 1、 Taylor, Nicholas J.,Emer, Enrico,Preshlock, Sean,Schedler, Michael,Tredwell, Matthew,Verhoog, Stefan,Mercier, Joel,Genicot, Christophe,Gouverneur, Véronique. "Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands". supporting information. p. 8267 - 8276. Retrieved 2017/06/27.
• 2、 Krishnamurthy, Byregowda,Vinaya, Kambappa,Rakshith, Devraj,Prasanna, Doddakunche Shivaramu,Rangappa, Kanchugarakoppal Subbegowda. "Synthesis of 3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a] pyrimidin-4-one derivatives as antibacterial agents". . p. 240 - 248. Retrieved 2013/07/28.