Butyl vinyl ether → 1-(6,6-Dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysen-12-yl)-ethanone

Temperature

90 °C

A solution of DMF/H2O (4:1) was de-gassed for 15 min. DMF/H2O (4:1, 6 ml) and 1-vinyloxy-butane (0.59 ml, 4.53 mmol) were added to a mixture of Pd(OAc)2 (6 mg, 26 μmol), 1,3-bis(diphenylphosphino)propane (24 mg, 57 K2CO3 (150 mg, 1.01 mmol), 12-bromo-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide 545 (370 mg, 0.91 mmol), under nitrogen. The mixture was heated at 90° C. for 2.5 h in the microwave. After cooling, the reaction was diluted with THF (2 ml) and 1M HCl (2 ml) and the mixture was stirred for 18 h. The mixture was further diluted with EtOAc (10 ml) and washed with water (10 ml, ×3). The precipitate formed during work-up was collected by filtration of the organic and aqueous phases and was found to be the title compound (140 mg, 40%). The organic phase was dried (Na2SO4) and concentrated in vacuo. The residue was triturated from MeOH to give the title compound (90 mg, 24%) which was used in the next step without further purification.

1. customA solution of DMF/H2O (4:1) was de-gassed for 15 min
2. temperatureAfter cooling
3. washwashed with water (10 ml, ×3)
4. customThe precipitate formed during work-up
5. filtrationwas collected by filtration of the organic and aqueous phases
6. dry with materialThe organic phase was dried (Na2SO4)
7. concentrationconcentrated in vacuo
8. customThe residue was triturated from MeOH

ORD record

ord-9cf66d933baa40a1ba1220de3821cd77

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102688B2