ethyl (5S)-7,7-dimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate

Base Information

• Chemical Name: ethyl (5S)-7,7-dimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate
• CAS No.: 1268251-96-2
• Molecular Formula: C₁₇H₂₁N₃O₂
• Molecular Weight: 299.373
• Mol file: 1268251-96-2.mol

Synonyms:ethyl (5S)-7,7-dimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate

Chemical Property of ethyl (5S)-7,7-dimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (5S)-7,7-dimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate

There total 3 articles about ethyl (5S)-7,7-dimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-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:

ethyl 7,7-dimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate (667920-79-8,667930-73-6,667930-74-7) → ethyl (5S)-7,7-dimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate (1268251-96-2) + ethyl (5R)-7,7-dimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate (1268251-95-1)

Guidance literature:

With CHIRALCEL OD; optical yield given as %ee; Resolution of racemate;

DOI:10.1021/jm101452x

Reference yield:

ethyl 7,7-dimethyl-5-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate (1260243-53-5) → ethyl (5S)-7,7-dimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate (1268251-96-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / ethanol / 0 - 20 °C

2: CHIRALCEL OD / Resolution of racemate

With sodium tetrahydroborate; In ethanol;

DOI:10.1021/jm101452x

Reference yield:

3-methyl-1-phenyl-but-2-en-1-one (5650-07-7) → ethyl (5S)-7,7-dimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate (1268251-96-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C

1.2: 2 h / 20 °C

2.1: sodium tetrahydroborate / ethanol / 0 - 20 °C

3.1: CHIRALCEL OD / Resolution of racemate

With sodium tetrahydroborate; sodium hydride; In ethanol; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jm101452x

upstream raw materials:

ethyl 7,7-dimethyl-5-phenyl-4,7-dihydropyrazolo[1,5-a]pyrimidine-3-carboxylate

ethyl 7,7-dimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylate

3-methyl-1-phenyl-but-2-en-1-one

Downstream raw materials:

(5S)-(-)-7,7-dimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[ 1,5-a]-pyrimidine-3-carboxylic acid

(5S)-(+)-N-[1-ethyl-1-(4-methylphenyl)propyl]-7,7-dimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide hydrochloride

(5S)-N-{1-ethyl-1-[4-(trifluoromethyl)phenyl]propyl}-7,7-dimethyl-5-phenyl-4,5,6-,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide