Sodium hydride → Diethyl [1-methyl-4-phenyl-5-(4-pyridyl)imidazol-2-yl]methoxylmethylphosphonate

HRID 479778Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 80% NaH in mineral oil (0.013 g, 0.452 mmol) in DMF at 0° C. was added 1-methyl-2-hydroxymethyl-4-phenyl-5-[4-pyridinyl]imidazole (0.100 g, 0.377 mmol) in DMF. The resulting bright yellow solution was stirred at 0° C. for 0.5 h when diethyl chloromethylphosphonate (0.070 mL, 0.452 mmol) dissolved in 0.079 mL of HMPA was added. The resulting mixture was stirred at 0° C. for 15 min and then warmed to rt. After 5 h, the solution was partitioned between CH2Cl2 and H2O. The organic extract was washed with aqueous NaCl and dried (MgSO4). The solvent was removed in vacuo, and the residue was purified by flash chromatography, eluting with 50:1 CH2Cl2/MeOH. The title compound was obtained as a light amber oil (0.088 g, 56%): ESMS (mnz): 416 (M++H).

Workup

additionwas added
temperaturewarmed to rt
waitAfter 5 h
customthe solution was partitioned between CH2Cl2 and H2O
extractionThe organic extract
washwas washed with aqueous NaCl
dry with materialdried (MgSO4)
customThe solvent was removed in vacuo
customthe residue was purified by flash chromatography
washeluting with 50:1 CH2Cl2/MeOH

Sources & evidence

ORD record: ord-6407d6b6c7664229be44fea43f14feee
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06645989B2

Reaction notes

Loading…