2-DIMETHYLAMINO-PYRIMIDINE-5-CARBALDEHYDE

2-(Dimethylamino)pyrimidine-5-carbaldehyde INTERMEDIATE 64 2-(Dimethylamino)pyrimidine-5-carbaldeh de 2-Chloropyrimidine-5-carbaldehyde (412mg, 2.89mmol) and EtGeneral procedure: Vilsmeier reagent was prepared by mixing ice-cold dry DMF (50 ml) and POCl3 (30.0 mmol, 2.8 ml). The mixture was stirred for 15 min at 25 °C. To the previous mixture, aminopyrimidines (10.0 mmol) in dry DMF (5.0 ml) were added over a period of 15 min at 0-5 °C. The reaction mixturewas stirred for 24 h at 25 °C.The mixture was then added to cold, saturated aq. K2CO3 andextracted with diethyl ether. The organic layer was washed withwater, dried over anhydrous Na2SO4, and evaporated underreduced pressure to afford the crude product, whichwas purified ina silica gel column chromatography using hexane/ethyl acetate(9:1) as an eluent to give the title compounds 2 and 8.(A)To a solution of 2-bromoacetic acid (40 g, 289.55 mmol, 1 eq) in DMF (125 ml) was added POCk (106 ml) dropwise at 0°C and the RM was stirred at 105°C for 8 h. The RM was quenched with EtOH (160 ml) dropwise at 0°C, followed by THF (800 ml). The RM was stirred at 0°C for 2 h. The precipitated crystalswere filtered off, washed with (20percent EtCH-THE) and dried under vacuum.(B) To a solution of 1 , 1-dimethylguanidine hydrochloride (10 g, 81.3 mmol, 1 eq) and the product from (A) (41.30 g, 162.6 mmol, 2 eq) in i-PrOAc (200 ml) was added a solution of KHCO3 (24.39 g, 243.9 mmol, 3 eq) in water (100 ml) in one portion at RT. The RM was stirred at RT for 48 h. The RM was diluted with water (100 ml), and the aq. layer was extracted with EtOAc (3x 100 ml), dried (Na2SO4) and concentratedto afford 2-(dimethylamino)pyrimidine-5-carbaldehyde (4.8 g, 39percent; over 2 steps).

Molecular Weight:151.17
XLogP3:0.1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:151.074561919
Monoisotopic Mass:151.074561919
Topological Polar Surface Area:46.1
Heavy Atom Count:11
Complexity:130
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes