1,2-Bis(bromomethyl)-4-nitrobenzene → HCID 59166727, compound

Butyllithium (0.29 ml, 0.74 mmol, 2.5 M) was added to a stirred solution of 4-chloro-5,7-dihydro-6H-pyrrolo [2,3-d]pyrimidin-6-one from Step B (50.0 mg, 0.295 mmol) at −78° C. in THF (30 mL). After complete addition of butyllithium, N,N,N′N′-tetramethylethane-1,2-diamine (0.31 mL, 0.77 mmol) was added. After 1 h at −78° C., 1,2-bis(bromomethyl)-4-nitrobenzene (91.0 mg, 0.295 mmol, described in Intermediate 4) was added and the reaction warmed to ambient temperature. After 8 h, the reaction was quenched with H2O (2 mL) and the mixture was partitioned between EtOAc (50 mL) and H2O (50 mL). The aqueous solution was extracted with EtOAc (3×20 mL). The combined organic extracts were washed with brine (100 mL), dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS: m/z=317 (M+1).

1. additionwas added
2. waitAfter 8 h
3. customthe reaction was quenched with H2O (2 mL)
4. customthe mixture was partitioned between EtOAc (50 mL) and H2O (50 mL)
5. extractionThe aqueous solution was extracted with EtOAc (3×20 mL)
6. washThe combined organic extracts were washed with brine (100 mL)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORD record

ord-467225a996324475919257f6bdadf403

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989624B2