ethyl 4-(bicyclo[1.1.1]pentan-1-ylamino)-2-(methylthio)pyrimidine-5-carboxylate

Base Information

• Chemical Name: ethyl 4-(bicyclo[1.1.1]pentan-1-ylamino)-2-(methylthio)pyrimidine-5-carboxylate
• CAS No.: 1403865-19-9
• Molecular Formula: C₁₃H₁₇N₃O₂S
• Molecular Weight: 279.363
• Mol file: 1403865-19-9.mol

Synonyms:ethyl 4-(bicyclo[1.1.1]pentan-1-ylamino)-2-(methylthio)pyrimidine-5-carboxylate

Chemical Property of ethyl 4-(bicyclo[1.1.1]pentan-1-ylamino)-2-(methylthio)pyrimidine-5-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 4-(bicyclo[1.1.1]pentan-1-ylamino)-2-(methylthio)pyrimidine-5-carboxylate

There total 1 articles about ethyl 4-(bicyclo[1.1.1]pentan-1-ylamino)-2-(methylthio)pyrimidine-5-carboxylate 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: 96.0%

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester (5909-24-0) + 1-aminobicyclo<1.1.1>pentane hydrochloride (22287-35-0) → ethyl 4-(bicyclo[1.1.1]pentan-1-ylamino)-2-(methylthio)pyrimidine-5-carboxylate (1403865-19-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In ethanol; at 20 ℃;

DOI:10.1021/acs.jmedchem.1c01716

Reference yield:

ethyl 4-(bicyclo[1.1.1]pentan-1-ylamino)-2-(methylthio)pyrimidine-5-carboxylate (1403865-19-9) → 4-(bicyclo[1.1.1]pentan-1-ylamino)-2-((trans)-4-hydroxycyclohexylamino)pyrimidine-5-carboxamide

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydroxide / ethanol; water / 20 °C

2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; acetonitrile / 1 h / 20 °C

2.2: 3.5 h / 20 °C / Reflux

3.1: N-(benzenesulfonyl)-3-phenyloxaziridine / chloroform / 20 °C

4.1: N,N-dimethyl-formamide / 100 - 110 °C / Inert atmosphere

With benzotriazol-1-ol; N-(benzenesulfonyl)-3-phenyloxaziridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; ethanol; chloroform; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/acs.jmedchem.1c01716

Reference yield:

ethyl 4-(bicyclo[1.1.1]pentan-1-ylamino)-2-(methylthio)pyrimidine-5-carboxylate (1403865-19-9) → 4-(bicyclo[1.1.1]pentan-1-ylamino)-2-(((1R,3S)-3-hydroxycyclohexyl)amino)pyrimidine-5-carboxamide

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydroxide / ethanol; water / 20 °C

2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; acetonitrile / 1 h / 20 °C

2.2: 3.5 h / 20 °C / Reflux

3.1: N-(benzenesulfonyl)-3-phenyloxaziridine / chloroform / 20 °C

4.1: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 100 °C

With benzotriazol-1-ol; N-(benzenesulfonyl)-3-phenyloxaziridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; chloroform; water; acetonitrile;

DOI:10.1021/acs.jmedchem.1c01716

upstream raw materials:

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester

1-aminobicyclo<1.1.1>pentane hydrochloride