Water → HCID 68978652, compound

4-Bromo-2-isopropyl-7-methylamino-2H-phthalazin-1-one (0.095 g, 0.32 mmol) was dissolved in DMF (5 ml). To this was added NaH (60%, 0.015 g, 0.38 mmol) as a suspension in DMF (2 ml). The mixture was stirred at RT for 30 min then chloroethyl methyl sulfide (0.042 g, 0.38 mmol) was added in one portion as a solution in DMF (1 ml) and the reaction mixture was heated to 70° C. for 24 hours. After this time, the reaction mixture was cooled to RT and water (10 ml) was added cautiously, the mixture was extracted with EtOAc (3×10 ml), the organic layers were combined, dried (MgSO4), filtered and concentrated under vacuum. Flash column chromatography (elution: 70% hexane, 30% EtOAc) gave the title compound (0.021 g, 18% yield) as a white solid. δH (400 MHz, CDCl3), 7.73 (1H, d), 7.48 (1H, d), 7.13 (1 H, d), 5.41-5.29 (1H, m), 3.71 (2H, t), 3.18 (3H, s), 3.15 (3H, s), 2.73 (2H, t), 1.41 (6H, d).

1. temperaturethe reaction mixture was heated to 70° C. for 24 hours
2. temperatureAfter this time, the reaction mixture was cooled to RT
3. extractionthe mixture was extracted with EtOAc (3×10 ml)
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated under vacuum
7. washFlash column chromatography (elution: 70% hexane, 30% EtOAc)

ORD record

ord-1860911f12d94f24bc465153aac55072

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07501410B2