Triethyl phosphite → HCID 12087790, compound

HRID 397367Notes

Reaction equation

[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[C:13]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:24]=3)[N+:12]=2[O-])=[CH:7][CH:6]=1)[CH3:3].P(OCC)(OCC)OCC>CN(C)C(=O)C>[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[NH:12][C:13]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:24]=3)=[C:14]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[N:15]=2)=[CH:9][CH:10]=1)[CH3:1]

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of 2-[4-(N,N-Dimethylaminomethyl)phenyl]-4-(4-fluorophenyl)-5-(2-phenoxy-4-pyrimidinyl)imidazole-N-oxide (0.32 g, 0.66 mmol) in 5 mL of N,N-dimethylacetamide was added triethyl phosphite (0.34 mL, 2.0 mmol) and the solution was heated at 95° C. overnight. The solution was concentrated to a small volume under reduced pressure and H2O was added. The mixture was extracted thrice with 20 mL of CH2C2. The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to give a yellow oil. The oil was purified by silica gel chromatography using 5-15% CH3OH/CH2Cl2 to give the title compound as a yellow foam (0.094 g, 30%). ES(+)MS m/e=466 (MH+)

Workup

concentrationThe solution was concentrated to a small volume under reduced pressure and H2O
additionwas added
extractionThe mixture was extracted thrice with 20 mL of CH2C2
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give a yellow oil
customThe oil was purified by silica gel chromatography

Sources & evidence

ORD record: ord-4befc091d52d4f8290ae4f96aa8dcbfb
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610695B1

Reaction notes

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