4,5-Pyrimidinediamine, 6-chloro-2-methyl- Chemical Properties

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

Appearance

Off-white to light yellow Solid

4,5-Pyrimidinediamine, 6-chloro-2-methyl- Usage And Synthesis

Uses

6-Chloro-2-methylpyrimidine-4,5-diamine is an intermediate in the synthesis of selective inhibitors of Class I Phosphatidylinositol 3-Kinases.

Synthesis

The general procedure for the synthesis of 6-chloro-2-methylpyrimidine-4,5-diamine from 2-methyl-4,6-dichloro-5-aminopyrimidine is as follows: 1. Preparation of 6-chloro-4,5-diamino-2-methylpyrimidine. To a 200 mL stainless steel Parr reactor was added 5-amino-4,6-dichloro-2-methylpyrimidine (7.2 g, 40 mmol) and an isopropanol solution of 2M ammonia (100 mL) and the reactor was sealed. The reaction mixture was heated at 150°C for 16 hours. Complete reaction was confirmed by HPLC analysis. After completion of the reaction, the mixture was concentrated under vacuum to obtain the residue. The residue was suspended in a solvent mixture of water (10 mL) and isopropanol (35 mL), stirred at 50°C for 1 hour, and then cooled to room temperature. The precipitate was collected by filtration, washed with a small amount of isopropanol and air dried over a filter to afford 6-chloro-4,5-diamino-2-methylpyrimidine (5.8 g, 91% yield) as a brown powder, which could be used in the next reaction without further purification.

References

[1] Patent: US2011/54173, 2011, A1. Location in patent: Page/Page column 21
[2] Patent: WO2009/144632, 2009, A1. Location in patent: Page/Page column 62
[3] Patent: WO2016/22890, 2016, A1. Location in patent: Page/Page column 64; 65
[4] Patent: WO2010/132598, 2010, A1. Location in patent: Page/Page column 75
[5] Patent: WO2011/25505, 2011, A1. Location in patent: Page/Page column 49

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