Sodium Fluoride → HCID 69464842, compound

HRID 1247842Notes

Reaction equation

HRID 1247842 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[CH3:12][N:13]([C:37]1[CH:38]=[N:39][N:40]([CH3:62])[C:41]=1[NH:42][C:43]([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:14](=O)[CH2:15][NH:16][C:17]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[F-].[Na+]>O>[CH3:12][N:13]([CH2:14][CH2:15][NH:16][C:17]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:37]1[CH:38]=[N:39][N:40]([CH3:62])[C:41]=1[NH:42][C:43]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

6

Reactant 4

HCID 5235Sodium FluorideHCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 21904495HCID 21904495, compound

Product 1

HCID 69464842HCID 69464842, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Lithium aluminum hydride (455 mg) was added slowly to tetrahydrofuran (40 ml) at 0° C. and the mixture was stirred for 20 minutes. N-Methyl-N-[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]-2-(tritylamino)acetamide (2 g) was added to the mixture at 0° C., and the whole mixture was stirred for 2 hours with warming to room temperature and refluxed for 2 hours. Sodium fluoride (2.51 g) and water (862 mg) were added to the mixture, and the whole mixture was stirred at room temperature for 30 minutes. The precipitate was filtered off, and the filtrate was concentrated under reduced pressure to give crude residue, which was chromatographed (silica gel; ethyl acetate:dichloromethane=1:10) to give N4,1-dimethyl-N5-trityl-N4-[2-(tritylamino)ethyl]-1H-pyrazole-4,5-diamine (740 mg).

Workup

  1. stirringthe whole mixture was stirred for 2 hours
  2. temperaturerefluxed for 2 hours
  3. stirringthe whole mixture was stirred at room temperature for 30 minutes
  4. filtrationThe precipitate was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto give crude residue, which
  7. customwas chromatographed (silica gel; ethyl acetate:dichloromethane=1:10)

Sources & evidence

ORD record
ord-c588142f8f5b4f17bc6fc0835f0418d6
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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