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

HRID 479778

반응식

HRID 479778 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 12679Hexamethylphosphoramide용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6407d6b6c7664229be44fea43f14feee
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06645989B2

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