(R)-Tert-butyl 4-(5-Methyl-6,7-dihydro-5H-cyclopenta[d]pyriMidin-4-yl)piperazine-1-carboxylate

Base Information

• Chemical Name: (R)-Tert-butyl 4-(5-Methyl-6,7-dihydro-5H-cyclopenta[d]pyriMidin-4-yl)piperazine-1-carboxylate
• CAS No.: 1001178-90-0
• Molecular Formula: C₁₇H₂₆N₄O₂
• Molecular Weight: 318.419
• Hs Code.: 2933399990
• Mol file: 1001178-90-0.mol

Synonyms:(R)-tertbutyl 4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate;(R)-tert-Butyl 4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate;(R)-Tert-butyl4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate;

Chemical Property of (R)-Tert-butyl 4-(5-Methyl-6,7-dihydro-5H-cyclopenta[d]pyriMidin-4-yl)piperazine-1-carboxylate

Chemical Property:

• Boiling Point: 455.6±45.0 °C(Predicted)
• PKA: 6.54±0.40(Predicted)
• PSA: 58.56000
• Density: 1.155±0.06 g/cm3(Predicted)
• LogP: 2.58630

Purity/Quality:

98%, ^*data from raw suppliers

(R)-tert-Butyl 4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-Tert-butyl 4-(5-Methyl-6,7-dihydro-5H-cyclopenta[d]pyriMidin-4-yl)piperazine-1-carboxylate

There total 10 articles about (R)-Tert-butyl 4-(5-Methyl-6,7-dihydro-5H-cyclopenta[d]pyriMidin-4-yl)piperazine-1-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: 86.0%

(R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine (953045-35-7) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → (R)-tert-butyl 4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]-pyrimidin-4-yl)piperazine-1-carboxylate (1001178-90-0)

Guidance literature:

In 1-methyl-pyrrolidin-2-one; at 110 ℃; Product distribution / selectivity;

Reference yield:

ethyl (2R)-2-methyl-5-(propan-2-ylidene)cyclopentanecarboxylate (623935-92-2) → (R)-tert-butyl 4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]-pyrimidin-4-yl)piperazine-1-carboxylate (1001178-90-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: ozone / ethyl acetate / 3.5 h / -68 °C

1.2: 0.5 h

2.1: ammonium acetate / methanol / 20 h / 20 °C / Inert atmosphere

3.1: 17 h / 150 °C

4.1: trichlorophosphate / 0.08 h / Reflux

5.1: triethylamine / butan-1-ol / Reflux; Inert atmosphere

With ammonium acetate; ozone; triethylamine; trichlorophosphate; In methanol; ethyl acetate; butan-1-ol;

Reference yield:

(2R)-2-methyl-5-oxocyclopentanecarboxylic acid ethyl ester (85440-74-0) → (R)-tert-butyl 4-(5-methyl-6,7-dihydro-5H-cyclopenta[d]-pyrimidin-4-yl)piperazine-1-carboxylate (1001178-90-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium hydroxide; water / ethanol / 10 h / Reflux

1.2: 0 °C

2.1: ammonium hydroxide / water / 3 h / Reflux

3.1: trichlorophosphate / 0.08 h / Reflux

4.1: triethylamine / butan-1-ol / Reflux; Inert atmosphere

With ammonium hydroxide; water; triethylamine; potassium hydroxide; trichlorophosphate; In ethanol; water; butan-1-ol;

upstream raw materials:

(R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine

1-t-Butoxycarbonylpiperazine

pulegone

ethyl (2R)-2-methyl-5-(propan-2-ylidene)cyclopentanecarboxylate

Downstream raw materials:

tert-butyl 4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]-pyrimidin-4-yl)piperazine-1-carboxylate

tert-butyl 4-((5R,7S)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate

(R)-tert-butyl 4-(5-methyl-7-oxo-6,7-dihydro-5H-cyclopenta[d]-pyrimidin-4-yl)piperazine-1-carboxylate

tert-butyl 4-((5R,7R)-5-methyl-7-((4-nitrobenzoyl)oxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-piperazine-1-carboxylate

Refernces

• 1、 Blake, James F.,Xu, Rui,Bencsik, Josef R.,Xiao, Dengming,Kallan, Nicholas C.,Schlachter, Stephen,Mitchell, Ian S.,Spencer, Keith L.,Banka, Anna L.,Wallace, Eli M.,Gloor, Susan L.,Martinson, Matthew,Woessner, Richard D.,Vigers, Guy P.A.,Brandhuber, Barbara J.,Liang, Jun,Safina, Brian S.,Li, Jun,Zhang, Birong,Chabot, Christine,Do, Steven,Lee, Leslie,Oeh, Jason,Sampath, Deepak,Lee, Brian B.,Lin, Kui,Liederer, Bianca M.,Skelton, Nicholas J.. "Discovery and preclinical pharmacology of a selective ATP-competitive Akt inhibitor (GDC-0068) for the treatment of human tumors". . p. 8110 - 8127. Retrieved 2012/11/13.
• 2、 -. "COMBINATIONS OF AKT INHIBITOR COMPOUNDS AND VEMURAFENIB, AND METHODS OF USE". Page/Page column 73-74. . Retrieved 2012/10/18.