5-BROMO-2-CHLORO-4-(METHYLTHIO)PYRIMIDINE

Preparation of 5-Bromo-2-chloro-4-methylsulfanyl-pyrimidine 5-Bromo-2-chloro-4-methylsulphanylpyrimidine Example 4.44; (RS)η(ethoxycarbonyl)-(4-{[4-{methylsulfanyl}-5-(thiophen-2-yl)-pyrimidin-2- yl]amino}phenyl)-S-methylsulfoximide; MeSNa (2 g, 28.5 mmol; 1 eq.) and 5-bromo-2, 4-dichloropyrimidine (6.5 g, 28.5 mmol, 1 eq.) are stirred in dry acetonitrile (50 mL) at rt for 24 h. Then the mixture is poured into water, extracted with DCM, dried (NaTo a stirring suspension of 5-bromo-2-chloro-4- (methylthio)pyrimidine (1.5 g, 6.26 mmol) in ethanol (7.5 mL) was added (lr, 4r)-4-amino-N, N- dimethylcyclohexanecarboxamide hydrochloride (1.618 g, 7.83 mmol) and DIEA (3.28 mL, 18.79 mmol). The resulting mixture was stirred at 80 C overnight. The ethanol was removed under reduced pressure and the remaining residue was purified using silica gel chromatography (0-90% ethyl acetate in hexanes) to afford (lr, 4r)-4-(5-bromo-4-(methylthio)pyrimidin-2-- 162 -ATI-2514175vl ylamino)-N, N-dimethylcyclohexanecarboxamide (1085 mg, 2.91 mmol, 46.4% yield). MS (ESI) m/z 373.0 [M+l]+, 375.2 [M+l]+.

Molecular Weight:239.52
XLogP3:2.7
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:237.89671
Monoisotopic Mass:237.89671
Topological Polar Surface Area:51.1
Heavy Atom Count:10
Complexity:116
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes