22632-10-6

Usage

Uses

Used in Pharmaceutical Industry:
4-Pyrimidinamine, N-methyl(9CI) is used as a key intermediate in the synthesis of various pharmaceuticals. It plays a crucial role in the production of antiviral drugs, which are essential for treating viral infections and diseases.
Used in Agrochemical Industry:
4-Pyrimidinamine, N-methyl(9CI) is also utilized in the synthesis of agrochemicals, specifically herbicides. Herbicides are chemicals used to control, kill, or inhibit the growth of unwanted plants, ensuring better crop yields and agricultural productivity.
Used in Organic Synthesis:
4-Pyrimidinamine, N-methyl(9CI) is an important intermediate in the synthesis of other organic compounds. Its versatile chemical properties make it a valuable building block for creating a wide range of chemical products, contributing to various industries.

Upstream product

• 89180-09-6 4-methylamino-1H-pyrimidine-2-thione 
• 52731-57-4 1,6-dihydro-6-imino-1-methylpyrimidine 
• 163133-86-6 pyrimidin-4-amine 
• 67-56-1 methanol 
• 7732-18-5 water 

Downstream Products

• 6104-45-6 3-methylpyrimidin-4-one 
• 84539-21-9 Methyl-(1-oxy-pyrimidin-4-yl)-amine 
• 56181-38-5 5-Brom-4-(N-methylamino)pyrimidin 

Relevant academic research and scientific papers

Efficient ruthenium-catalyzed N-methylation of amines using methanol

An in situ-generated complex from [RuCpCl2]2 and dpePhos ligand is reported as an efficient catalyst in the presence of 5 mol % of LiOtBu for the N-methylation of amines using methanol as the methylating agent at moderate conditions, following hydrogen borrowing strategy. This simple catalyst system provides selective N-monomethylation of substituted primary anilines and sulfonamides as well as N,N dimethylation of primary aliphatic amines in excellent yields at 40-100 °C with good tolerance to reducible functional groups. The catalytic intermediate CpRu(dpePhos)H was isolated and was shown to be active for methylation in the absence of base.

On the Chichibabin Amination of Pyrimidine and N-Alkylpyrimidinium Salts Using Liquid Ammonia/Potassium Permanganate

Treatment of the 2-R-pyrimidines (1, R = methyl, ethyl, i-propyl and t-butyl) with potassium amide/liquid ammonia/potassium permanganate leads to amination at C-4(6).The yields of the 4(6)-amino compounds 3 increase in the order 2-methyl (10percent), 2-ethyl (30percent), 2-i-propyl (45percent) and 2-t-butyl (60percent).Treatment of the 2-R-N-methylpyrimidinium salts (4, R = hydrogen, methyl) with liquid ammonia/potassium permanganate leads to a regiospecific imination at C-6, the corresponding 2-R-1,6-dihydro-6-imino-1-methylpyrimidines 6 being obtained in 80-85percent yield.It is proved by 15N-labelling that no ring opening is involved in these imination reactions.Treatment of the imino compounds with base leads to the corresponding 2-R-6-methylaminopyrimidines 8, involving, as proved by 15N-labelling, an ANRORC-mechanism. 2-t-Butyl-1-ethylpyrimidinium tetrafluoroborate (9b) when treated with liquid ammonia/potassium permanganate undergoes N-deethylation, 2-t-butylpyrimidine being exclusively formed.