(R)-2-[4-(2-aminopyrimidin-5-yl)phenyl]-2-cyclopropylpropionitrile

Base Information

• Chemical Name: (R)-2-[4-(2-aminopyrimidin-5-yl)phenyl]-2-cyclopropylpropionitrile
• CAS No.: 1360552-08-4
• Molecular Formula: C₁₆H₁₆N₄
• Molecular Weight: 264.33
• Mol file: 1360552-08-4.mol

Synonyms:(R)-2-[4-(2-aminopyrimidin-5-yl)phenyl]-2-cyclopropylpropionitrile

Chemical Property of (R)-2-[4-(2-aminopyrimidin-5-yl)phenyl]-2-cyclopropylpropionitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[4-(2-aminopyrimidin-5-yl)phenyl]-2-cyclopropylpropionitrile

There total 5 articles about (R)-2-[4-(2-aminopyrimidin-5-yl)phenyl]-2-cyclopropylpropionitrile 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: 51.0%

5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyrimidin-2-ylamine (402960-38-7) + (R)-2-(4-bromo-phenyl)-2-cyclopropylpropionitrile (1360551-90-1) → (R)-2-[4-(2-aminopyrimidin-5-yl)phenyl]-2-cyclopropylpropionitrile (1360552-08-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In N,N-dimethyl-formamide; at 90 ℃; for 0.333333h; Inert atmosphere; Microwave irradiation; Sealed tube;

DOI:10.1021/jm501185j

Reference yield:

2-(4-bromo-phenyl)-2-cyclopropylpropionitrile (1360551-88-7) → (R)-2-[4-(2-aminopyrimidin-5-yl)phenyl]-2-cyclopropylpropionitrile (1360552-08-4)

Guidance literature:

Multi-step reaction with 2 steps

1: carbon dioxide / ethanol / Resolution of racemate

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran / 24 h / 80 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbon dioxide; sodium carbonate; In tetrahydrofuran; ethanol;

Reference yield:

(4-bromophenyl)(cyclopropyl)methanone (6952-89-2) → (R)-2-[4-(2-aminopyrimidin-5-yl)phenyl]-2-cyclopropylpropionitrile (1360552-08-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrahydrofuran; diethyl ether / 2.16 h / -78 - 20 °C

2.1: boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -78 °C

2.2: 2 h / -78 - 20 °C

3.1: carbon dioxide / ethanol / Resolution of racemate

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran / 24 h / 80 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbon dioxide; boron trifluoride diethyl etherate; sodium carbonate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;

upstream raw materials:

(4-bromophenyl)(cyclopropyl)methanone

5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyrimidin-2-ylamine

(R)-2-(4-bromo-phenyl)-2-cyclopropylpropionitrile

1-(4-bromophenyl)-1-cyclopropylethan-1-ol

Downstream raw materials:

5-[4-((R)-1-{5-[1-(2-aminoethyl)-1H-pyrazol-4-yl]-[1,2,4]oxadiazol-3-yl}-1-cyclopropylethyl)phenyl]pyrimidin-2-ylamine

5-[4-((R)-1-cyclopropyl-1-{5-[1-(2-dimethylaminoethyl)-1H-pyrazol-4-yl]-[1,2,4]oxadiazol-3-yl}-ethyl)phenyl]pyrimidin-2-ylamine

2-[4-(3-{(1R)-1-[4-(2-aminopyrimidin-5-yl)phenyl]-1-cyclopropylethyl}-1,2,4-oxadiazol-5-yl)-1H-pyrazol-1-yl]-N,N-dimethylacetamide

5-(4-{(R)-1-cyclopropyl-1-[5-(1H-pyrazol-4-yl)-[1,2,4]oxadiazol-3-yl]ethyl}phenyl)pyrimidin-2-ylamine