2-(Methylthio)-4-pyrimidinecarboxaldehyde

2-(methylthio)pyrimidine-4-carbaldehyde (4): 4-(dimethoxymethyl)-2-(methylthio)pyrimidine (3) (53.7 g, 268 mmol) was added carefully to 1.2 N aqueous HCl (300 mL, 268 mmol, 1.0 equiv.) and stirred at 60° C. for 3 hours. The reaction mixture was then cooled to room temperature and neutralized by the slow addition of solid sodium bicarbonate. The crude mixture was extracted with diethyl ether (3.x.150 mL) and the combined organic layer was concentrated under reduced pressure to afford 2-(methylthio)pyrimidine-4-carbaldehyde (4) as a yellow solid (14.2 g, 41.5 g theoretical, 34percent). LC-MS m/z 155 (M+1). Reference: WO 2006/009734 A1, pg 67.4-(dimethoxymethyl)-2- (methylthio)pyrimidine (3) (53.7 g, 268 mmol) was added carefully to 1 .2 N aqueous HCl (300 mL, 268 mmol, 1 .0 equiv.) and stirred at 60°C for 3hours. The reaction mixture was then cooled to room temperature and neutralized by the slow addition of solid sodium bicarbonate. The crude mixture was extracted with diethyl ether (3 x 1 50 mL) and the combined organic layer was concentrated under reduced pressure to afford 2- (methylthio)pyrimidine-4-carbaldehyde (4) as a yellow solid ( 14.2 g, 41.5 g theoretical, 34percent). LC-MS m/z 1 55 (M+ 1 ). Reference: W2006009734A 1 , pg 67.2-(methylthio)pyrimidine-4-carbaldehyde(6): 4-(dimethoxymethyl)-2-(methylthio)pyrimidine(5) (53.7 g, 268 mmol) was added carefully to 1.2 N aqueous HCl (300 mL, 268 mmol, 1.0 equiv.) and stirred at 60°C for 3 hours. The reaction mixture was then cooled to room temperature and neutralized by the slow addition of solid sodiumbicarbonate. The crude mixture wasextracted with diethyl ether (3 x 150 mL) and the combined organic layer was concentrated under reduced pressure to afford 2-(methylthio)pyrimidine-4-carbaldehyde (6) as a yellow solid (14.2g, 41.5 g theoretical, 34percent). LC-MSm/z 155 (M+1).c) b b b

Molecular Weight:154.19
XLogP3:0.8
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:154.02008399
Monoisotopic Mass:154.02008399
Topological Polar Surface Area:68.2
Heavy Atom Count:10
Complexity:120
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes