Stannous chloride dihydrate → HCID 136347864, compound

Temperature

0 °C

To a suspension of 6-aminoquinazolin-4(3H)-one (3.07 g, 19.0 mmol, 1.0 eq) in conc. HCl (30.0 ml) at 0° C. was added dropwise NaNO2 (1.51 g, 21.9 mmol, 1.15 eq) as a solution in H2O (20.0 ml). The resulting mixture was stirred at 0° C. for 1 h, and then treated with a solution of SnCl2.2H2O (18.5 g, 81.9 mmol, 4.30 eq) in conc. HCl (20.0 ml). The reaction was stirred at 0° C. for 1 h and then at RT for 2 h. The reaction was diluted with EtOH (200 ml), treated with 4,4-dimethyl-3-oxopentanenitrile (3.10 g, 24.8 mmol, 1.30 eq), heated at reflux overnight, then cooled to RT and concentrated. The residue was diluted with EtOAc (100 mL), then stirred in an ice/H2O bath and made basic (pH 8) with solid NaOH. The mixture was filtered through Celite®, washed with H2O (50 mL) and then EtOAc (100 mL). The organic phase was washed with brine, dried (Na2SO4) and concentrated to yield a yellow solid, which was triturated from Et2O (100 ml) to yield 6-(5-amino-3-t-butyl-1H-pyrazol-1-yl)quinazolin-4(3H)-one (1.2 g, 22% yield). MS (ESI) m/e (M+H+) 284.2

1. stirringThe reaction was stirred at 0° C. for 1 h
2. waitat RT for 2 h
3. temperatureheated
4. temperatureat reflux overnight
5. temperaturecooled to RT
6. concentrationconcentrated
7. additionThe residue was diluted with EtOAc (100 mL)
8. stirringstirred in an ice/H2O bath
9. filtrationThe mixture was filtered through Celite®
10. washwashed with H2O (50 mL)
11. washThe organic phase was washed with brine
12. dry with materialdried (Na2SO4)
13. concentrationconcentrated
14. customto yield a yellow solid, which
15. customwas triturated from Et2O (100 ml)

ORD record

ord-fee1e28753504e98b3cbdf634a093030

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163756B2