2-Chloro-5-(cyclopropylmethoxy)pyrimidine

A) 2-chloro-5-(cyclopropylmethoxy)pyrimidine To a solution of cyclopropylmethanol (276 mg), 2-chloropyrimidin-5-ol (500 mg) and triphenylphosphine (1.51 g) in toluene (20 mL) was added dropwise diisopropyl azodicarboxylate toluene solution (1.9 M, 3 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (659 mg). 80.0 mg (0.28 mmol) of the amine VII.1, 55.8 mg (0.28 mmol) of example XII.4 and 144 muL (0.84 mmol) DIPEA in 2 mL NMP are stirred at 100 C. for 30 min. The reaction mixture is directly purified by HPLC (ACN/H2O/NH3).For example 6.7 the reaction conditions are 150 C. over night.A) General procedure: 0.80 mg (6.13 mmol) 2-chloro-5-hydroxypyrimidine, 1.26 g (9.19 mmol) 1-bromo-2-methylpropane and 1.69 g (12.26 mmol) K2CO3 are added to 10 mL DMF and stirred at 80 C. over night. Afterwards the reaction is quenched by the addition of water and extracted with EtOAc. The org. layers are combined, dried over MgSO4, filtered and the solvent is removed in vacuo.C8H11ClN2O (M=186.6 g/mol)ESI-MS: 187 [M+H]+Rt (HPLC): 1.04 min (method D)General procedure: Example XII.1 (general route) -Chloro-5-/'so-butoxy-pyrimidine 0.80 mg (6.13 mmol) 2-chloro-5-hydroxypyrimidine, 1 .26 g (9.19 mmol) 1-bromo-2- methylpropane and 1.69 g (12.26 mmol) K2C03 are added to 10 mL DMF and stirred at 80 C over night. Afterwards the reaction is quenched by the addition of water and extracted with EtOAc. The org. layers are combined, dried over MgSO4, filtered and the solvent is removed in vacuo. C8H11CIN2O(M= 186.6 g/mol) ESI-MS: 187 [M+H]+ Rt (HPLC):1.04 min (method D)

Molecular Weight:184.62
XLogP3:1.9
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:184.0403406
Monoisotopic Mass:184.0403406
Topological Polar Surface Area:35
Heavy Atom Count:12
Complexity:144
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes