Dinitrofluorobenzene → HCID 86593641, compound

HRID 1822623Notes

Reaction equation

HRID 1822623 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:46][CH3:47])=[C:5]([CH:43]=[CH:44][CH:45]=1)[C:6]([O:19][CH2:20][C@H:21]1[O:25][C@@H:24]([N:26]2[CH:33]=[CH:32][C:30](=[O:31])[NH:29][C:27]2=[O:28])[C@H:23]([O:34][NH:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C@@H:22]1[OH:42])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N+:48]([C:51]1[CH:56]=[C:55]([N+:57]([O-:59])=[O:58])[CH:54]=[CH:53][C:52]=1F)([O-:50])=[O:49]>CO>[CH3:1][O:2][C:3]1[C:4]([O:46][CH3:47])=[C:5]([CH:43]=[CH:44][CH:45]=1)[C:6]([O:19][CH2:20][C@H:21]1[O:25][C@@H:24]([N:26]2[CH:33]=[CH:32][C:30](=[O:31])[NH:29][C:27]2=[O:28])[C@H:23]([O:34][N:35]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[C:52]2[CH:53]=[CH:54][C:55]([N+:57]([O-:59])=[O:58])=[CH:56][C:51]=2[N+:48]([O-:50])=[O:49])[C@@H:22]1[OH:42])([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6264Dinitrofluorobenzene3×HCID 86593642HCID 86593642, compound

Product 1

HCID 86593641HCID 86593641, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5′-O-(dimethoxytrityl)-2′-O-(hexylamino)uridine (0.88 grams, 1.37 mmol) was dissolved in methanol (20 mL). 2,4-Dinitrofluorobenzene (DNFB, 0.25 grams, 1.37 mmol) was added and the mixture shaken on a mechanical shaker. The reaction was monitored by TLC. After 90 min, another 0.25 grams of DNFB was added and the reaction mixture shaken an additional 30 min, followed by addition of another 0.25 grams of DNFB. After shaking 2.5 hours, the mixture was concentrated in vacuo and chromatographed on a silica gel column, eluting with a gradient of 25% ethyl acetate in hexanes to 100% ethyl acetate. The desired product (0.51 grams, 46%) eluted with 100% ethyl acetate (Rf 0.85 by TLC).

Workup

  1. stirringthe reaction mixture shaken an additional 30 min
  2. stirringAfter shaking 2.5 hours
  3. concentrationthe mixture was concentrated in vacuo
  4. customchromatographed on a silica gel column
  5. washeluting with a gradient of 25% ethyl acetate in hexanes to 100% ethyl acetate
  6. washThe desired product (0.51 grams, 46%) eluted with 100% ethyl acetate (Rf 0.85 by TLC)

Sources & evidence

ORD record
ord-93f60bc4618a4890a4f09cf6666fa213
Source dataset
uspto-grants-2006_05
Patent number
US07037646B1

Reaction notes

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