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

HRID 538244Notes

Reaction equation

[Cl:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:21]=[CH: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)[CH:21]=[CH: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 (32.9 mg, 0.25 mmol) was added to a stirred solution of 6-(4-fluoro-phenyl)-2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one (75 mg, 0.22 mmol) in DMF (3.5 mL). The mixture was stirred at 150° C. for 15 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 20/80). The desired fractions were collected and the solvents evaporated in vacuo. The product was triturated with DIPE to yield 3-chloro-6-(4-fluoro-phenyl)-2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one (46 mg, 56% yield) as a white solid. 1H NMR (400 MHz, CDCl3) 8 ppm 5.12 (s, 2H), 6.62 (d, J=7.9 Hz, 1H), 6.98 (tt, J=7.4, 0.9 Hz, 1H), 7.03-7.07 (m, 2H), 7.06 (d, J=7.6 Hz, 1H), 7.17-7.25 (m, 2H), 7.27-7.34 (m, 2H), 7.35-7.43 (m, 2H).

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
customThe product was triturated with DIPE

Sources & evidence

ORD record: ord-416023b8c36c48a2b56ec5e2aabd9953
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865725B2

Reaction notes

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