Hydrochloric Acid → N-(3-chloro-4-fluorophenyl)-5,8-dihydro-6H-spiro[1-benzothieno[2,3-d]pyrimidine-7,2'-[1,3]dioxolan]-4-amine

To a stirring ethanol solution (100 mL) of 4-chloro-5,8-dihydro-6H-spiro[1-benzothieno[2,3-d]pyrimidine-7,2′-[1,3]dioxolane] (7.0 g, 24.8 mmol) was added 4-fluoro-3-chloroaniline (3.6 g, 24.8 mmol) and 0.05 mL 4N HCl (in dioxane). The contents were heated to reflux for 5 h, after which time the contents were removed from heating and allowed to cool to rt. The solvent was removed under reduced pressure, the crude residue suspended in aq. NaHCO3 (100 mL), and stirred for 15 min. The contents were again filtered, and the solid filter cake washed with water. The collected yellow solid was triturated with diethyl ether (50 mL) to afford the final product (5.5 g, 57%) as a light yellow solid. 1H-NMR (DMSO-d6) δ 8.41 (s, 1H), 8.28 (s, 1H), 7.78 (dd, 1H), 7.58 (m, 1H), 7.35 (t, 1H), 3.97 (s, 4H), 3.22 (t, 2H), 3.00 (s, 2H), 1.93 (t, 2H); LCMS RT=3.26 min; [M+H]+=392.3.

1. temperatureThe contents were heated
2. temperatureto reflux for 5 h
3. customafter which time the contents were removed
4. temperaturefrom heating
5. customThe solvent was removed under reduced pressure
6. filtrationThe contents were again filtered
7. filtrationthe solid filter cake
8. washwashed with water
9. customThe collected yellow solid was triturated with diethyl ether (50 mL)

ORD record

ord-ce858db1a0c644e58109e4cc24910b6f

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07238701B2