Description
4,6-Dimethyl-2-hydroxypyrimidine (4,6-DHP) is a synthetic pyrimidine analogue classified as a functional nutritional compound[6]. The hydrochloride salt serves as a precursor for synthesizing 4,6-dimethyl-2-chloropyrimidine via reaction with phosphorus oxychloride[4]. It acts as a ligand in coordination chemistry, reacting with copper(II) perchlorate in aqueous ammonia to form [(NH3)2Cu(dmpymo)](ClO4)·2H2O, and with palladium complexes to yield [(dach)Pd(2-dmpymo)]4(NO3)4[5][7].
Chemical Properties
Off-white, light yellow to pink crystalline powder
Uses
4,6-Dimethyl-2-hydroxypyrimidine is a component of Nicarbazine (N394530), a coccidiostat, which is an antiprotozoal agent that acts upon Coccidia parasites.
Synthesis
IM06: Synthesis of 4,6-dimethylpyrimidin-2-one
Step 1: Urea (20.0 g, 333.3 mmol) and acetylacetone (33.3 g, 333.3 mmol) were dissolved in ethanol (166 mL), followed by the slow addition of concentrated aqueous hydrochloric acid solution (45 mL). The reaction mixture was stirred at 80 °C for 24 hours. Upon completion of the reaction, the mixture was cooled to room temperature, the precipitate was collected by filtration and washed with cold ethanol to afford 4,6-dimethylpyrimidin-2-ol as a colorless solid (40 g, 97% yield). The product was characterized by 1H NMR (DMSO-d6, 400 MHz): δ 7.35 (1H, s), 2.43 (6H, s).
Purification Methods
Crystallise the pyrimidine from absolute EtOH (charcoal). [Beilstein 24/2 V 138.]
References
[1] Patent: US2013/5743, 2013, A1. Location in patent: Page/Page column 12
[2] Patent: WO2013/4617, 2013, A1. Location in patent: Page/Page column 30
[3] European Journal of Inorganic Chemistry, 2018, vol. 2018, # 23, p. 2695 - 2701
