4-methyl-2-phenyl-6-(pyrazol-1-ylmethyl)pyrimidine

Base Information

• Chemical Name: 4-methyl-2-phenyl-6-(pyrazol-1-ylmethyl)pyrimidine
• CAS No.: 131291-63-9
• Molecular Formula: C₁₅H₁₄N₄
• Molecular Weight: 250.303

Synonyms:4-methyl-2-phenyl-6-(pyrazol-1-ylmethyl)pyrimidine

Chemical Property of 4-methyl-2-phenyl-6-(pyrazol-1-ylmethyl)pyrimidine

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Technology Process of 4-methyl-2-phenyl-6-(pyrazol-1-ylmethyl)pyrimidine

There total 2 articles about 4-methyl-2-phenyl-6-(pyrazol-1-ylmethyl)pyrimidine 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: 97.0%

NH-pyrazole (288-13-1) + 4-chloromethyl-6-methyl-2-phenylpyrimidine (131291-62-8) → 4-methyl-2-phenyl-6-(pyrazol-1-ylmethyl)pyrimidine (131291-63-9)

Guidance literature:

With potassium hydroxide; tetra(n-butyl)ammonium hydroxide; In benzene; for 5h; Heating;

DOI:10.1016/0022-328X(90)85300-N

Reference yield:

4,6-dimethyl-2-phenylpyrimidine (14164-34-2) → 4-methyl-2-phenyl-6-(pyrazol-1-ylmethyl)pyrimidine (131291-63-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 37 percent Spectr_. / N-chlorosuccinimide, benzoyl peroxide / CCl₄ / 20 h / Heating

2: 97 percent / 40percent aq. KOH, 40percent aq. tetrabutyl ammonium hydroxide / benzene / 5 h / Heating

With potassium hydroxide; N-chloro-succinimide; Perbenzoic acid; tetra(n-butyl)ammonium hydroxide; In tetrachloromethane; benzene;

DOI:10.1016/0022-328X(90)85300-N

upstream raw materials:

NH-pyrazole

4-chloromethyl-6-methyl-2-phenylpyrimidine

4,6-dimethyl-2-phenylpyrimidine

Refernces

Cyclometallated compounds VI. Cyclopalladation of 2-phenylpyrimidines with pendant pyrazole donors

10.1016/0022-328X(90)85300-N

The research investigates the potential of pendant pyrazole groups to induce double cyclopalladation of 2-phenylpyrimidines. The study aimed to explore whether the addition of extra nitrogen donors at the 4- and 6-positions of the pyrimidine ring could facilitate double cyclopalladation of a 2-phenyl-pyrimidine, a process that was previously resistant in simpler substrates. The researchers synthesized and tested various 2-phenylpyrimidines with different substituents to observe their cyclopalladation behavior. The key chemicals used in this process included 4,6-bis(pyrazol-1-yl)-2-phenylpyrimidine, 4-methyl-2-phenyl-6-(pyrazol-1-ylmethyl)pyrimidine, and 4,6-bis(pyrazol-1-ylmethyl)-2-phenylpyrimidine, along with lithium tetrachloropalladate as the palladium source. The conclusions drawn from the study were that while 4,6-bis(pyrazol-1-yl)-2-phenylpyrimidine underwent only monocyclopalladation, 4-methyl-2-phenyl-6-(pyrazol-1-ylmethyl)pyrimidine reacted preferentially to give a cyclopalladated regioisomer with tridentate coordination, and 4,6-bis(pyrazol-1-ylmethyl)-2-phenylpyrimidine resulted in a mixture of both singly and doubly cyclopalladated products. This research provides insights into the influence of ligand structure on the cyclopalladation process and contributes to the understanding of cyclometallation reactions.

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