The origin of a common compound about 2-(4,6-Dichloropyrimidin-5-yl)acetaldehyde

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16019-33-3, its application will become more common.

Synthetic Route of 16019-33-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 16019-33-3 as follows.

Step 1 : 7-(4-Bromo-3-fluorophenyl)-4-chloro-6,7-dihydro-5H-pyrrolo[2,3- c/]pyrimidine (141) A round bottom flask was charged with 4-bromo-3-fluoroaniline (10.0 g, 52.5 mmol) and then cooled to -150C. Trifluoroacetic acid (50 ml.) was added to the above cold aniline while stirring the contents for 0.5 h. Na(OAc)3BH (15.9 g, 50 mmol) was added portion wise to the above mixture and stirred for additional 0.5 h. The aldehyde 209 (see example 118, step 1 , 7.85 g, 75 mmol) in CH2CI2 (15 ml.) was added to the above mixture. The resultant mixture was allowed to warm up to the ambient temperature and stirred for 24 h. The reaction mixture was concentrated under reduced pressure and the residue was poured into sat. NaHCO3 solution (250 ml.) and then the mixture was extracted with CH2CI2 (3 x 250 ml_). The combined organic layer was washed with brine (1 x 100 ml_), dried over sat. Na2SO4 and then concentrated under reduced pressure to afford crude material, which was recrystallized from CH2CI2 and MeOH to afford 8.65 g (53%) of the title prodcuct 141_as an off-white solid. 1H NMR (400 MHz, DMSO-c/6): delta 8.42 (s, 1 H), 7.88 and 7.86 (dd, J1 = 11.2 Hz, J2 = 2.8 Hz, 2 H), 7.51 (t, J = 8.0 Hz, 1 H), 7.36 and 7.34 (dd, J1 = 9.2 Hz, J2 = 2.4 Hz, 1 H), 4.11 (t, J = 8.8 Hz, 2 H), 3.22 (t, J = 8.4 Hz, 2 H); LCMS (ESI): m/z 329 (M + H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16019-33-3, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/8895; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia