Sodium hydride → HCID 131717244, compound

HRID 466684Notes

Reaction equation

HRID 466684 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:12]=[CH:11][N:10]=[C:9]2[C:5]=1[NH:6][C:7]([CH2:13][CH2:14][CH3:15])=[N:8]2.[C:16]1([C:22]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[N:23]2[C:27]([C:28]3[C:33]([C:34]4[CH:39]=[CH:38][C:37]([CH2:40]Br)=[CH:36][CH:35]=4)=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:26][N:25]=[N:24]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[Cl:3][C:4]1[N:12]=[CH:11][N:10]=[C:9]2[C:5]=1[N:6]=[C:7]([CH2:13][CH2:14][CH3:15])[N:8]2[CH2:40][C:37]1[CH:36]=[CH:35][C:34]([C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:27]2[N:23]([C:22]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:24]=[N:25][N:26]=2)=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 190122236-Chloro-8-propyl-9H-purine

Product 1

HCID 131717244HCID 131717244, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of NaH (0.016 g of a 60% dispersion in oil, 0.4 mmol) in dry dimethylformamide (1.5 ml) was added 6-Chloro-8-propylpurine (0.044 g, 0.25 mmol) at room temperature. After 20 minutes, the mixture was cooled to 0° C. and N-triphenylmethyl-5-(4'-bromomethylbiphen-2-yl)tetrazole (0.139 g, 0.25 mmol) was added. The resulting mixture was warmed to room temperature and then stirred at 40° C. for 3 hours. The reaction was cooled, and the content of the flask was poured into ice-water (50 ml) and extracted with ethyl acetate (3×15 ml). The combined organic phase was washed with brine and then dried over anhydrous Na2SO4. Removal of the solvent gave the crude product as a foam which was purified by flash-chromatography on silica-gel using ethyl acetate/hexane (1:3).

Workup

  1. temperatureThe resulting mixture was warmed to room temperature
  2. temperatureThe reaction was cooled
  3. extractionextracted with ethyl acetate (3×15 ml)
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-3172d536e6bc4fafb15ea02aeadc4d87
Source dataset
uspto-grants-1992_10
Patent number
US05157026

Reaction notes

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