Chlorotrimethylsilane → HCID 178470311, compound

Temperature

80 °C

To a solution of ethyl 2-(2-carbamoyl-5-chlorophenylamino)-2-oxoacetate (545 mg, 2.02 mmol) and TEA (11 mL, 80 mmol) in DCE (20 mL) was added trimethylsilyl chloride (3.8 mL, 30 mmol) and the solution was stirred at 80° C. for 16 h. The mixture was concentrated under reduced pressure and the residue was partitioned between saturated aq NaHCO3 and DCM (100 mL). The separated aqueous phase was extracted with DCM (2×100 mL) and the combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 10-60% EtOAc/hexanes to afford ethyl 7-chloro-4-hydroxyquinazoline-2-carboxylate as a solid (321 mg, 63%). 1H NMR (300 MHz, DMSO-d6) δ 1.36 (t, J=7.06 Hz, 3H), 4.39 (q, J=7.10 Hz, 2H), 7.60-7.74 (m, 1H), 7.85-7.98 (m, 1H), 8.11-8.23 (m, 1H), 12.82 (br s, 1H).

1. concentrationThe mixture was concentrated under reduced pressure
2. customthe residue was partitioned between saturated aq NaHCO3 and DCM (100 mL)
3. extractionThe separated aqueous phase was extracted with DCM (2×100 mL)
4. dry with materialthe combined organic layers were dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel chromatography
8. washeluting with 10-60% EtOAc/hexanes

ORD record

ord-e62e9e8f292b446ab97adacc431c0308

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09308207B2