N,N'-Dimethylethylenediamine → 6-(4-fluoro-phenyl)-2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one

HRID 538241Notes

Reaction equation

[O:1]([CH2:8][C:9]1[N:10]=[C:11]2[CH:16]=[CH:15][NH:14][C:13](=[O:17])[N:12]2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23](I)=[CH:22][CH:21]=1.C([O-])([O-])=O.[K+].[K+].CNCCNC>C1(C)C=CC=CC=1.[Cu]I>[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:14]2[CH:15]=[CH:16][C:11]3=[N:10][C:9]([CH2:8][O:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:18][N:12]3[C:13]2=[O:17])=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Copper(I)iodide (11.8 mg, 0.062 mmol) was added to a stirred suspension of 2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one (50 mg, 0.21 mmol), 4-fluoroiodobenzene (72.5 mg, 0.41 mmol), K2CO3 (57 mg, 0.41 mmol) and N,N′-dimethylethylenediamine (0.011 mL, 0.1 mmol) in toluene (1 mL) in a sealed tube. The mixture was stirred at 120° C. for 16 hours. The mixture was filtered through a pad of diatomaceous earth and then the solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM with a gradient of 0/100 to 30/70). The desired fractions were collected and evaporated in vacuo to yield 6-(4-fluoro-phenyl)-2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one (45 mg, 65% yield) as a white solid. 1H NMR (500 MHz, CDCl3) 8 ppm 5.20 (s, 2H), 6.70 (d, J=7.8 Hz, 1H), 6.98 (t, J=7.2 Hz, 1H), 7.03 (d, J=8.1 Hz, 2H), 7.12 (d, J=7.8 Hz, 1H), 7.19-7.25 (m, 2H), 7.27-7.34 (m, 2H), 7.38-7.45 (m, 2H), 7.83 (s, 1H).

Workup

filtrationThe mixture was filtered through a pad of diatomaceous earth
customthe solvent was evaporated in vacuo
customThe crude product was purified by flash column chromatography (silica
customThe desired fractions were collected
customevaporated in vacuo

Sources & evidence

ORD record: ord-8b18a1dc91f6443bb7ea5e55bc0ebe5f
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865725B2

Reaction notes

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