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

HRID 479778

反応式

HRID 479778 の反応式
[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]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 76633Phosphonic acid, P-(chloromethyl)-, diethyl esterHCID 187715292-Hydroxymethyl-1-methyl-4-phenyl-5-(4-pyridyl)imidazole

生成物 1

HCID 86587538Diethyl [1-methyl-4-phenyl-5-(4-pyridyl)imidazol-2-yl]methoxylmethylphosphonate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 12679Hexamethylphosphoramide溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-6407d6b6c7664229be44fea43f14feee
出典データセット
uspto-grants-2003_11
特許番号
US06645989B2

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