5151-34-8

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dimethoxy-5-methylpyrimidine is used as an intermediate compound for the synthesis of various pharmaceutical products. Its unique structure allows it to be a key component in the development of new drugs, contributing to the advancement of medicine.
Used in Biochemical Research:
In the field of biochemical research, 2,4-Dimethoxy-5-methylpyrimidine is utilized as a research tool to study the structure and function of nucleic acids and their derivatives. Its presence in RNA and DNA makes it a valuable asset for understanding the molecular basis of genetic information.
Used in Organic Synthesis:
2,4-Dimethoxy-5-methylpyrimidine is employed as a building block in organic synthesis, allowing chemists to create a wide range of complex molecules with potential applications in various industries. Its versatility in chemical reactions makes it a sought-after compound for the synthesis of novel organic compounds.

Upstream product

• 1780-31-0 2,6-dichloro-5-methylpyrimidine 
• 124-41-4 sodium methylate 
• 96606-05-2 5-methyl-6-chloro-2,4-dimethoxypyrimidine 
• 3551-55-1 2,4-dimethoxypyrimidine 
• 74-88-4 methyl iodide 
• 65-71-4 thymin 
• 25902-89-0 4-methoxy-5-methyl-pyrimidin-2(1H)-one 
• 77-78-1 dimethyl sulfate 
• 56686-16-9 5-bromo-2,4-dimethoxypyrimidine 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 25902-87-8 4-methoxy-1,5-dimethyl-2(1H)-pyrimidinone 
• 65-71-4 thymin 
• 7323-83-3 4-methoxy-5-methyl-1-(tri-O-benzoyl-β-D-ribofuranosyl)-1H-pyrimidin-2-one 
• 52606-02-7 2,4-dimethoxy-5-pyrimidine carboxaldehyde 
• 2140-61-6 5-methylcytidine 
• 4160-72-9 1-methylthymine 
• 80504-53-6 5-methyl-1-(2'-O-p-tolylsulfonylethoxymethyl)uracil 
• 68724-11-8 1-[(2-hydroxyethoxy)methyl]thymine 
• 80955-99-3 1-(2-O-acetyl-3-deoxy-3-trifluoroacetamido-5-O-p-nitrobenzoyl-β-D-ribofuranosyl)-4-methoxy-5-methyl-1,2-dihydropyrimidin-2-one 
• 80504-45-6 1,2-dihydro-5-methyl-4-methoxy-2-oxo-1-(2'-benzoyloxyethoxymethyl)pyrimidine 

Relevant academic research and scientific papers

Deprotonative metalation of aromatic compounds by using an amino-based lithium cuprate

Deprotonative cupration of aromatic compounds by using amino-based lithium cuprates was optimized with 2,4-dimethoxypyrimidine and 2-methoxypyridine as the substrates and benzoyl chloride as the electrophile. [(tmp)2CuLi] (+2 LiCl) (tmp=2,2,6,6-tetramethylpiperidino) was identified as the best reagent and its use was extended to anisole, 1,4-dimethoxybenzene, other substituted pyridines, furan, thiophene and derivatives, and N-Boc-indole (Boc=tert-butyloxycarbonyl). Of the electrophiles employed to attempt the interception of the generated aryl cuprates, aroyl chlorides, iodomethane, and diphenyl disulfide efficiently reacted. In addition, different oxidative agents were identified to afford symmetrical biaryls. Finally, palladium-catalyzed coupling with aryl halides was optimized and allowed the synthesis of different aryl derivatives in medium to good yields.

New Gilman-type lithium cuprate from a copper(II) salt: synthesis and deprotonative cupration of aromatics

Deprotonative cupration of aromatics including heterocycles (anisole, 1,4-dimethoxybenzene, thiophene, furan, 2-fluoropyridine, 2-chloropyridine, 2-bromopyridine, and 2,4-dimethoxypyrimidine) was realized in tetrahydrofuran at room temperature using the Gilman-type amido-cuprate (TMP)2CuLi in situ prepared from CuCl2·TMEDA through successive addition of 1 equiv of butyllithium and 2 equiv of LiTMP. The intermediate lithium (hetero)arylcuprates were evidenced by trapping with iodine, allyl bromide, methyl iodide, and benzoyl chlorides, the latter giving the best results. Symmetrical dimers were also prepared from lithium azine and diazine cuprates using nitrobenzene as an oxidative agent.

Oxidative amination of cuprated pyrimidine and purine derivatives

Using regioselective cuprations (via magnesiations), various primary, secondary and tertiary aminated pyrimidine and purine derivatives were prepared by the oxidative coupling of lithium amidocuprates using chloranil. DNA and RNA units such as aminated uracil or thymine, and adenine, as well as a CDK inhibitor, purvalanol A, were all obtained under mild conditions and satisfactory yields.

HSAB-driven chemoselective N1-alkylation of pyrimidine bases and their 4-methoxy- or 4-acetylamino-derivatives

The lithium salts of the conjugated bases of 4-methoxy- and 4-acetylamino-2(1H)-pyrimidinones 1-3 undergo highly chemoselective N1-methylation or ethylation when treated with methyl- or ethylsulfate (hard electrophiles) in dry dioxane, while the use of DMF as solvent results in competitive O2-alkylation. Potassium salts of the same bases in DMF undergo prevalent O2-attack. Under the same conditions, a similar but less chemoselective behaviour is observed in alkylation of thymine and uracil, where some N3-attack occurs. This can be rationalised in terms of the HSAB principle.