Chlorosuccinimide → 4,6-Dichloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine

HRID 1432194Notes

Reaction equation

[Cl:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl:18]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[C:9]([Cl:18])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4-chloro-5-(4-fluorophenyl)thieno[2,3-d]pyrimidine (1 g, 4.06 mmol) in acetic acid (15 mL), N-chlorosuccinimide (1.08 g, 8.1 m. mol) was added and the mixture was stirred at 90° C. for 2 h. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate (30 mL) and washed with sat. NaHCO3 solution (3×20 mL). The organic layer was dried over sodium sulfate and evaporated. The crude product was purified by column chromatography to get the title product (200 mg, 16%) as pale yellow solid. 1H NMR (400 MHz, CDCl3 and CDCl3): δ 8.85 (s, 1H), 7.35 (m, 2H), 7.20 (m, 2H). MS (ESI) m/z: Calculated: 297.95; Observed: 299.2 (M++1).

Workup

customThe solvent was evaporated under reduced pressure
dissolutionthe residue was dissolved in ethyl acetate (30 mL)
washwashed with sat. NaHCO3 solution (3×20 mL)
dry with materialThe organic layer was dried over sodium sulfate
customevaporated
customThe crude product was purified by column chromatography

Sources & evidence

ORD record: ord-d4aef522161d4cb682222ae3d759ee8b
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612078B2

Reaction notes

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