Sodium Carbonate → 5-(4-Amino-3-cyclohex-1-enyl-phenyl)-tetrahydro-pyrimidin-2-one

[2-Bromo-4-(2-oxo-hexahydro-pyrimidin-5-yl)-phenyl]-carbamic acid tert-butyl ester (99 mg, 0.26 mmol, as prepared in the previous step) was dissolved in TFA (1 mL). The resulting mixture was stirred at RT for 30 min and concentrated in vacuo. The residue obtained was dried in vacuo for 1 h and dissolved in EtOH (0.5 mL) and toluene (1 mL). To this solution cyclohex-1-enyl boronic acid (20.5 mg, 0.16 mmol), 2M Na2CO3 (0.5 mL, 1 mmol) and Pd (PPh3)4 (30 mg, 0.025 mmol) were added. The resulting mixture was heated at 80° C. overnight. The reaction mixture was allowed to cool to RT and extracted with EtOAc (2×10 mL). The EtOAc layers were combined, dried (Na2SO4) and concentrated in vacuo. The residue obtained was purified on silica (2% MeOH-EtOAc) to afford the title compound (31 mg) contaminated with Ph3PO, which was used in the next step without further purification: Mass spectrum (ESI, m/z): Calcd. for C16H21N3O, 272.1 (M+H), found 272.1.

1. concentrationconcentrated in vacuo
2. customThe residue obtained
3. customwas dried in vacuo for 1 h
4. dissolutiondissolved in EtOH (0.5 mL)
5. temperatureThe resulting mixture was heated at 80° C. overnight
6. temperatureto cool to RT
7. extractionextracted with EtOAc (2×10 mL)
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated in vacuo
10. customThe residue obtained
11. customwas purified on silica (2% MeOH-EtOAc)

ORD-Eintrag

ord-3c0a8e2cc15b4e90a07e76bd3adcc083

Quelldatensatz

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08481564B2