241483-00-1Relevant articles and documents
An improved process for the synthesis of DMTMM-based coupling reagents
Raw, Steven A.
, p. 946 - 948 (2009)
A simple, robust and high-yielding process for the preparation of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium tetrafluoroborate (DMTMM BF4) and hexafluorophosphate (DMTMM PF6) has been developed, which avoids the use of expensive or unusual reagents.
An Efficient Synthesis of Pemetrexed Disodium
Qi,Wen,Li,Bai,Chen,Wang
, p. 1565 - 1569 (2015/10/06)
An efficient synthetic method for the pemetrexed disodium has been developed using methyl 4-iodobenzoate and 3-buten-1-ol as starting materials via six steps. The developed process avoided some tedious workup procedures and unfriendly reagents compared with the reported synthetic routes. In addition, two impurities generated in the process were isolated and characterized by 1H NMR, 13C NMR, and HRMS. The mechanisms of the two impurities were also discussed, and the impurities could be easily removed by suitable workup procedures. The overall yield of pemetrexed disodium was increased from 12.8% (literature) to 34.9%. Therefore, this cost-effective, environmental friendly, and high-yielding process is more suitable for scale-up production of pemetrexed disodium.
Transformation of tertiary amines into alkylating reagents by treatment with 2-chloro-4,6-dimethoxy-1,3,5-triazine. A synthetic application of side-reaction accompanying coupling by means of 4-(4,6-dimethoxy-[1,3,5] triazin-2-yl)-4-methyl-morpholin-4-ium chloride (DMTMM)
Kolesinska,Kaminski
experimental part, p. 2115 - 2123 (2009/04/07)
Mild reaction conditions are described for the preparation of a number of alkyl chlorides and 2-dialkyl(aryl)amino-4,6-dirnethoxy-1,3,5-triazines by dealkylation of quaternary triazinylammonium chlorides formed as reactive intermediates in reaction of tertiary amines with 2-chloro-4,6-dimethoxy-1,3,5- triazine. The high selectivity of substitution was observed within the reactivity order of the alkyl groups: benzyl ~ allyl > methyl > n-alkyl. Studies on dealkylation of S-(-)-J-dimethyl-(1-phenylethyl)amine to R-(+)-1-chloro-1-phenylethane revealed that reaction proceeded with an inversion of configuration on the carbon atom as may be expected for SN2 type substitution. The scope of reaction was extended by exchange of anion in quaternary triazinylammonium chlorides with 1-, SCN-, C6H5O-, CH3COO- followed by N-dealkylation step.