6-[1-(2,6-difluorophenyl)ethyl]-3,4-dihydro-5-methyl-2-thioxopyrimidin-4(3H)-one

Base Information

• Chemical Name: 6-[1-(2,6-difluorophenyl)ethyl]-3,4-dihydro-5-methyl-2-thioxopyrimidin-4(3H)-one
• CAS No.: 255898-86-3
• Molecular Formula: C₁₃H₁₂F₂N₂OS
• Molecular Weight: 282.314
• Mol file: 255898-86-3.mol

Synonyms:6-[1-(2,6-difluorophenyl)ethyl]-3,4-dihydro-5-methyl-2-thioxopyrimidin-4(3H)-one

Chemical Property of 6-[1-(2,6-difluorophenyl)ethyl]-3,4-dihydro-5-methyl-2-thioxopyrimidin-4(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-[1-(2,6-difluorophenyl)ethyl]-3,4-dihydro-5-methyl-2-thioxopyrimidin-4(3H)-one

There total 10 articles about 6-[1-(2,6-difluorophenyl)ethyl]-3,4-dihydro-5-methyl-2-thioxopyrimidin-4(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: 65.0%

thiourea (17356-08-0) + ethyl 4-(2,6-difluorophenyl)-2,4-dimethyl-3-oxobutanoate (359828-74-3) → 6-[1-(2,6-difluorophenyl)ethyl]-3,4-dihydro-5-methyl-2-thioxopyrimidin-4(3H)-one (255898-86-3)

Guidance literature:

With ethanol; sodium; for 12h; Inert atmosphere; Reflux;

DOI:10.1021/acs.jmedchem.5b01979

Reference yield: 40.0%

thiourea (17356-08-0) + ethyl 4-(2,6-difluorophenyl)-2,4-dimethyl-3-oxobutanoate (359828-74-3) → 6-(1-(2,6-difluorophenyl)ethyl)-5-methyl-3,4-dihydro-2-thioxopyrimidin-4(3H)-one (255898-86-3)

Guidance literature:

With sodium ethanolate; In ethanol; for 5h; Heating;

DOI:10.1021/jm010853h

Reference yield:

2,6-difluorophenylacetic acid (85068-28-6) → 6-[1-(2,6-difluorophenyl)ethyl]-3,4-dihydro-5-methyl-2-thioxopyrimidin-4(3H)-one (255898-86-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1.25 h / -10 - 20 °C

1.2: 74 percent / hexane; tetrahydrofuran / 0.25 h / -10 - 20 °C

2.1: thionyl chloride / 2 h / Heating

3.1: Et₃N; MgCl₂ / acetonitrile / 2 h / 20 °C

3.2: acetonitrile / 2 h / Heating

4.1: aq. HCl / 0.25 h / 25 °C

5.1: 40 percent / NaOEt / ethanol / 5 h / Heating

With hydrogenchloride; n-butyllithium; thionyl chloride; sodium ethanolate; triethylamine; magnesium chloride; In tetrahydrofuran; ethanol; hexane; acetonitrile;

DOI:10.1021/jm0507330

upstream raw materials:

thiourea

ethyl 4-(2,6-difluorophenyl)-2,4-dimethyl-3-oxobutanoate

2,6-difluorophenylacetic acid

(2RS)-2-(2,6-difluorophenyl)propanoic acid

Downstream raw materials:

6-[(1R)-1-(2,6-difluorophenyl)ethyl]-2-[(1S,2S)-2-(4-methoxyphenyl)cyclopropylmethylsulfanyl]-5-methyl-3H-pyrimidin-4-one

6-[(1S)-1-(2,6-difluorophenyl)ethyl]-2-[(1S,2S)-2-(4-methoxyphenyl)cyclopropylmethylsulfanyl]-5-methyl-3H-pyrimidin-4-one