Stannous chloride dihydrate → HCID 68181739, compound

Temperature

60 °C

To a solution of 4-N-(5-bromo-4-fluoro-2-nitrophenyl)pyrimidine-2,4-diamine (713 mg, 2.17 mmol) in ethanol (30 mL) was added tin(II) chloride dihydrate (1.72 g, 7.61 mmol) The reaction mixture was stirred at 60° C. for 1 hr. Upon completion, reaction mixture was evaporated to dryness and added to ice water (20 mL). The pH was adjusted to pH10 using sat Na2CO3 solution (30 mL) and EtOAc (30 mL) was added. Saturated Rochelle's salt (20 mL) was added and the mixture stirred until separate layers were observed. The organic layer was separated and the aqueous layer extracted with EtOAc (2×5 mL). Combined organics were washed with saturated Rochelles salt (15 mL) followed by brine solution (15 mL) and dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound as a pale orange solid (500 mg, 68.7% yield); 1H NMR (250 MHz, DMSO) delta 8.11 (s, 1H), 7.75 (d, J=5.7 Hz, 1H), 7.37 (d, J=7.6 Hz, 1H), 6.67 (d, J=11.1 Hz, 1H), 6.08 (s, 2H), 5.75 (d, J=5.7 Hz, 1H), 5.37 (s, 2H); LC-MS: m/z+299.75 (M+H)+.

1. customUpon completion, reaction mixture
2. customwas evaporated to dryness
3. additionadded to ice water (20 mL)
4. additionwas added
5. additionSaturated Rochelle's salt (20 mL) was added
6. stirringthe mixture stirred
7. customuntil separate layers
8. customThe organic layer was separated
9. extractionthe aqueous layer extracted with EtOAc (2×5 mL)
10. washCombined organics were washed with saturated Rochelles salt (15 mL)
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated in vacuo

ORD record

ord-5e2bdc18faa04a868ed44c549a0b4453

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901313B2