61044-96-0

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-5-methyl-2-(methylthio)pyrimidine is used as a key reactant in the preparation of 1,2-dihydropyrimido[4,5-c]pyridazine-based inhibitors for lymphocyte-specific kinase (Lck). These inhibitors play a crucial role in the development of targeted therapies for the treatment of autoimmune diseases and inflammatory conditions by modulating the activity of Lck, a non-receptor tyrosine kinase involved in the regulation of immune cell signaling.
Additionally, due to its reactivity and structural features, 4-chloro-5-methyl-2-(methylthio)pyrimidine can be further modified and utilized in the synthesis of other bioactive molecules, contributing to the advancement of drug discovery and development in the pharmaceutical industry.

InChI:InChI=1/C6H7ClN2S/c1-4-3-8-6(10-2)9-5(4)7/h3H,1-2H3

Upstream product

• 20651-30-3 2-methylthio-3,4-dihydro-5-methylpyrimidin-4-one 
• 20651-30-3 5-methyl-2-(methylthio)pyrimidin-4-ol 
• 636-26-0 5-methyl-2-thiouracil 

Downstream Products

• 54308-64-4 5-methyl-2-methylthiopyrimidin-4-amine 
• 532931-23-0 4-(o-carboxyphenylamino)-5-methyl-2-methylthiopyrimidine 
• 18588-37-9 5-methylpyrimidine-2,4-diamine 
• 909095-75-6 2-(4-chloro-2-methylsulfanylpyrimidin-5-yl)-1-(2,6-dichlorophenyl)ethanone 
• 909095-77-8 3-(2,6-dichlorophenyl)-1,2-dimethyl-7-methylsulfanyl-1,2-dihydropyrimido[4,5-c]pyridazine 
• 909095-76-7 1-(2,6-dichloro-phenyl)-2-[4-(N,N'-dimethyl-hydrazino)-2-methylsulfanyl-pyrimidin-5-yl]-ethanone 
• 909095-79-0 4-(2,6-dichlorophenyl)-8-methylsulfanyl-1,2-dihydro-3a,7,9,9b-tetraazacyclopenta[a]naphthalen-3-one 
• 909095-78-9 1-{5-[2-(2,6-dichlorophenyl)-3-oxoethyl]-2-methylsulfanylpyrimidin-4-yl}pyrazolidin-3-one 
• 916907-11-4 4-(2,6-dichlorophenyl)-4-hydroxy-8-methylsulfanyl-1,2,4,5-tetrahydro-3a,7,9,9b-tetraazacyclopenta[a]naphthalen-3-one 
• 909095-82-5 4-(2,6-dichlorophenyl)-8-methylsulfinyl-1,2-dihydro-3a,7,9,9b-tetraazacyclopenta[a]naphthalen-3-one 
• 916907-13-6 1-(2-chloro-5-methoxyphenyl)-2-(4-chloro-2-methylsulfanylpyrimidin-5-yl)ethanone 
• 916907-14-7 1-{5-[2-(2-chloro-5-methoxyphenyl)-2-oxoethyl]-2-methylsulfanylpyrimidin-4-yl}pyrazolidin-3-one 
• 916907-15-8 4-(2-chloro-5-methoxyphenyl)-8-methylsulfanyl-1,2-dihydro-3a,7,9,9b-tetraazacyclopenta[a]naphthalen-3-one 
• 916907-17-0 4-(2-chloro-5-methoxyphenyl)-8-[4-(4-methylpiperazin-1-yl)-phenylamino]-1,2-dihydro-3a,7,9,9b-tetraazacyclopenta[a]naphthalen-3-one 

Relevant academic research and scientific papers

SELECTIVE INHIBITORS AGAINST Cdk4 AND Cdk6 HAVING AMINOTHIAZOLE SKELETON

The present invention relates to a compound represented by Formula [I]: wherein X is O, S, NH or CH 2 ; Y 1 , Y 2 , Y 3 , Y 4 and Y 5 , which may be identical or different, are each CH or N; however, at least one of Y 1 , Y 2 , Y 3 , Y 4 and Y 5 is N; Z 1 and Z 2 , which may be identical or different, are each CH or N; n is an integer from 1 to 3; R 1 is a C 3 -C 8 cycloalkyl group, a C 6 -C 10 aryl group, an aliphatic heterocyclic ring or an aromatic heterocyclic ring, or a bicyclic aliphatic saturated hydrocarbon group; R 2 and R 3 , which may be identical or different, are each a hydrogen atom, a lower alkyl group, a lower alkenyl group, a C 3 -C 8 cycloalkyl group, a C 6 -C 10 aryl group, an aromatic heterocyclic ring, or the like; and R 4 is a hydrogen atom, a lower alkyl group, a C 3 -C 6 cycloalkyl group or the like, or a pharmaceutically acceptable salt or ester thereof, and a selective inhibitor against Cdk4 and/or Cdk6 or an anticancer agent containing the compound or a pharmaceutically acceptable salt or ester thereof.

Reactions with 2-thiothymine; selective cyclization of S-substituted 2-thiothymine

2-Thiothymine (I) undergoes S-alkylation when treated with some halo compounds such as methyl and ethyl iodides. The S-alkyl derivatives II are treated with hydrazine hydrate to produce the hydrazine derivative III, which condensed with p-chlorobenzaldehyde to give p-chlorobenzaldehydepyrimidinehydrazone derivative IV. Compound IIa reacts with phosphorus oxychloride to give 4-chloro derivative V. The chlorine atom in V undergoes nucleophilic substitution with p-chloroaniline and anthranilic acid to produce drivatives VIa,b. Dehydrative cyclization of VIb yields the pyrimido[6,1-b]quinazolin-10-one derivative VII. Treatment of V with ammonia solution gives the diamino derivative VId. Reaction of V with sodium azide produces the tetrazolo[1,5-c]pyrimidine derivative VIII. Compound I undergoes S-alkylation with α-haloketones followed by cyclization to produce the thiazolo[3,2-a]pyrimidine derivatives Xa-c. Reaction of I with bromomalononitrile produces thiazolo[3,2-a]pyrimidine-2-carbonitrile derivative XII. Treatment of XII with formic acid, formamide and ammonium thiocyanate produces thiazolo[3,2-a:4,5-d]dipyrimidine derivatives XIIIa-c. Finally, reacting XII with malononitrile yields ppyrido[2′,3′:4,5]thiazolo[3,2-a]pyrimidine-3-carbonitrile derivative XIV.