Chlorosuccinimide → 3-chloro-6-(4-fluoro-phenyl)-2-phenoxymethyl-7,8-dihydro-6H-imidazo[1,2-c]pyrimidin-5-one

HRID 538251Notes

Reaction equation

[Cl:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:21][CH2:20][C:19]3=[N:22][C:23]([CH2:25][O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:24][N:18]3[C:17]2=[O:33])=[CH:12][CH:11]=1>CN(C=O)C>[Cl:1][C:24]1[N:18]2[C:17](=[O:33])[N:16]([C:13]3[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=3)[CH2:21][CH2:20][C:19]2=[N:22][C:23]=1[CH2:25][O:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 150 °C

Procedure

N-chlorosuccinimide (30.5 mg, 0.23 mmol) was added to a stirred solution of 6-(4-fluoro-phenyl)-2-phenoxymethyl-7,8-dihydro-6H-imidazo[1,2-c]pyrimidin-5-one (0.1 g, 0.3 mmol) in DMF (3.25 mL). The mixture was stirred at 150° C. for 20 minutes under microwave irradiation. The solvent was evaporated in vacuo and the crude product was purified by flash column chromatography (silica; AcOEt in DCM with a gradient of 0/100 to 15/85). The desired fractions were collected and the solvents evaporated in vacuo to yield 3-chloro-6-(4-fluoro-phenyl)-2-phenoxymethyl-7,8-dihydro-6H-imidazo[1,2-c]pyrimidin-5-one (21 mg, 27% yield) as a white solid. 1H NMR (400 MHz, CDCl3) 8 ppm 3.27 (t, J=6.6 Hz, 2H), 3.99 (t, J=6.6 Hz, 2H), 4.99 (s, 2H), 6.95-7.01 (m, 1H), 7.01-7.07 (m, 2H), 7.09-7.17 (m, 2H), 7.27-7.36 (m, 4H).

Workup

customThe solvent was evaporated in vacuo
customthe crude product was purified by flash column chromatography (silica
customThe desired fractions were collected
customthe solvents evaporated in vacuo

Sources & evidence

ORD record: ord-68cf4e4f8e3041b5987455181ce7d7be
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865725B2

Reaction notes

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