7-benzyl-10-(2-Methylbenzyl)-2,6,7,8,9,10-hexahydroiMidazo[1,2-a]pyrido[4,3-d]pyriMidin-5(3H)-one

Base Information

• Chemical Name: 7-benzyl-10-(2-Methylbenzyl)-2,6,7,8,9,10-hexahydroiMidazo[1,2-a]pyrido[4,3-d]pyriMidin-5(3H)-one
• CAS No.: 41276-02-2
• Molecular Formula: C24H26 N4 O
• Molecular Weight: 386.497
• Mol file: 41276-02-2.mol

Synonyms:NSC350625

Chemical Property of 7-benzyl-10-(2-Methylbenzyl)-2,6,7,8,9,10-hexahydroiMidazo[1,2-a]pyrido[4,3-d]pyriMidin-5(3H)-one

Chemical Property:

• Vapor Pressure: 1.46E-12mmHg at 25°C
• Boiling Point: 559.7°Cat760mmHg
• Flash Point: 292.3°C
• PSA: 42.53000
• Density: 1.24g/cm³
• LogP: 1.85260
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble2mg/mL, clear (warmed)

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,6,7,8,9,10-Hexahydro-10-[(2-methylphenyl)methyl]-7-(phenylmethyl)-imidazo[1,2-a]pyrido[4,3-d]pyrimidin-5(3H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,6,7,8,9,10-Hexahydro-10-[(2-methylphenyl)methyl]-7-(phenylmethyl)-imidazo[1,2-a]pyrido[4,3-d]pyrimidin-5(3H)-one is a small molecule TRAIL gene induction by normal and tumor cells as an anticancer t herapy. 2,6,7,8,9,10-Hexahydro-10-[(2-methylphenyl)methyl]-7-(phenylmethyl)-imidazo[1,2-a]pyrido[4,3-d]pyrimidin-5(3H)-one is a small molecule TRAIL gene induction by normal and tumor cells as an anticancer therapy. The compound identified as NSC 350625 was assigned the structure above for many years. The compound is correctly characterized as B285480. The resolution of this issue was recently highlighted in Chemical and Engeneering News 92(23) 32 (2014).

Technology Process of 7-benzyl-10-(2-Methylbenzyl)-2,6,7,8,9,10-hexahydroiMidazo[1,2-a]pyrido[4,3-d]pyriMidin-5(3H)-one

There total 5 articles about 7-benzyl-10-(2-Methylbenzyl)-2,6,7,8,9,10-hexahydroiMidazo[1,2-a]pyrido[4,3-d]pyriMidin-5(3H)-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: 87.0%

10-(2-methylbenzyl)-2,3,6,7,8,9-hexahydroimidazo[1,2-a]pyrido[4,3-d]pyrimidin-5(10H)-one (41642-16-4) + benzaldehyde (100-52-7) → 7-benzyl-10-(2-methylbenzyl)-2,6,7,8,9,10-hexahydroimidazo[1,2-a]pyrido[4,3-d]pyrimidin-5(3H)-one (41276-02-2)

Guidance literature:

With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1002/anie.201402133

Reference yield:

(4-chloropyridin-3-yl)(2-(methylthio)-4,5-dihydro-1H-imidazol-1-yl)methanone (1616632-78-0) → 7-benzyl-10-(2-methylbenzyl)-2,6,7,8,9,10-hexahydroimidazo[1,2-a]pyrido[4,3-d]pyrimidin-5(3H)-one (41276-02-2)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium phosphate / N,N-dimethyl acetamide / 1 h / Inert atmosphere; Reflux

2: hydrogen; platinum(IV) oxide / methanol; trifluoroacetic acid / 5 h

3: sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere

With platinum(IV) oxide; potassium phosphate; hydrogen; sodium tris(acetoxy)borohydride; acetic acid; In methanol; dichloromethane; N,N-dimethyl acetamide; trifluoroacetic acid;

DOI:10.1002/anie.201402133

Reference yield:

4-chloronicotinic acid chloride hydrochloride → 7-benzyl-10-(2-methylbenzyl)-2,6,7,8,9,10-hexahydroimidazo[1,2-a]pyrido[4,3-d]pyrimidin-5(3H)-one (41276-02-2)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / dichloromethane / 19 h / 0 - 20 °C / Inert atmosphere

2: potassium phosphate / N,N-dimethyl acetamide / 1 h / Inert atmosphere; Reflux

3: hydrogen; platinum(IV) oxide / methanol; trifluoroacetic acid / 5 h

4: sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere

With platinum(IV) oxide; potassium phosphate; hydrogen; sodium tris(acetoxy)borohydride; acetic acid; triethylamine; In methanol; dichloromethane; N,N-dimethyl acetamide; trifluoroacetic acid;

DOI:10.1002/anie.201402133

upstream raw materials:

10-(2-methylbenzyl)-2,3,6,7,8,9-hexahydroimidazo[1,2-a]pyrido[4,3-d]pyrimidin-5(10H)-one

benzaldehyde

(4-chloropyridin-3-yl)(2-(methylthio)-4,5-dihydro-1H-imidazol-1-yl)methanone

4-chloronicotinic acid

Refernces

• 1、 Jacob, Nicholas T.,Lockner, Jonathan W.,Kravchenko, Vladimir V.,Janda, Kim D.. "Pharmacophore reassignment for induction of the immunosurveillance cytokine TRAIL". . p. 6628 - 6631. Retrieved 2014/07/08.