3-N-Boc-amino-azetidine

white powder

A mixture of (113 mg, 0.33 mmol) and 10percent Pd/C (88 mg) in ethanol (3 ml) was stirred under hydrogen atmosphere at rt for 2 h. The reaction mixture was filtered and evaporated to give XXA (63 mg) as a white solid.To a solution of tetrahydro-4H-pyran-4-one (1.162 g, 11.6 mmol) in DCM (50 ml) was added tert-butyl azetidin-3-ylcarbamate (1 g, 5.8 mmol). The mixture was stirred at r.t. for 2 hours. Then to the mixture was added NaBH (OAc) 3 (3.687 g, 17.4 mmol). The mixture was stirred at r.t. overnight. The mixture was diluted with DCM (200 ml), washed with brine (200 ml 2), dried over Na 2SO 4, concentrated. The residue was purified by chromatography column on silica with eluent of MeOH/DCM = 1/20 (v/v) to give the product (800 mg) as a yellow oil. MS (ESI, m/e) [M+1] + 257.1.A solution of N-[1 -(5-{2-[(dimethylamino)methyl]phenyl}thiophen-2-yl)ethyl]-6-fluoro-2- methylpyrido[3, 4-d]pyrimidin-4-amine (3.00 g, 7.12 mmol), tert-butyl azetidin-3- ylcarbamate (3.68 g, 21 .4 mmol) and triethylamine (5.0 ml_, 36 mmol) in DMSO (70 ml_) was stirred at 120 over the weekend. The reac tion mixture was poured into H2O (250 ml_) and stirred at room temperature during 10 minutes (formation of a brown gunk). The solvent was poured out and the viscous solid dried in vacuo to give the title compound. LC-MS (Method 10): m/z: [M+H]+ = 574, Rt = 1 .46 min.

Molecular Weight:172.22
XLogP3:0.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:172.121177757
Monoisotopic Mass:172.121177757
Topological Polar Surface Area:50.4
Heavy Atom Count:12
Complexity:170
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes