Potassium Carbonate → HCID 19811545, compound

HRID 373241Notes

Reaction equation

HRID 373241 reaction equation
[Cl:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH2:9][CH3:10])[C:4](=[O:11])[CH:3]=1.Br[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26]2[N:30]([C:31]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:29]=[N:28][N:27]=2)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[N:7]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[N:30]([C:31]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[N:29]=[N:28][N:27]=3)=[CH:18][CH:19]=2)[C:6](=[O:8])[N:5]([CH2:9][CH3:10])[C:4](=[O:11])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6408456-chloro-3-ethylpyriMidine-2,4(1H,3H)-dioneHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazole

Product 1

HCID 19811545HCID 19811545, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-chloro-3-ethylpyrimidine-2,4(1H,3H)-dione (0.5 g), 4-bromomethyl-2'-(N-trityltetrazol-5-yl)biphenyl (1.68 g) and potassium carbonate (0.48 g) in DMF (20 ml) was stirred at room temperature for 20 hours. The reaction mixture was concentrated to dryness in vacuo and then the residue was dissolved in methylene chloride. The insoluble material was removed from the reaction mixture by filtration and the filtrate was concentrated to dryness. The resulting residue was purified by column chromatography on silica gel to give colorless amorphous powders (1.3 g, 70%).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness in vacuo
  2. dissolutionthe residue was dissolved in methylene chloride
  3. customThe insoluble material was removed from the reaction mixture by filtration
  4. concentrationthe filtrate was concentrated to dryness
  5. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-528bcb727b8847be8a4e53ded56e9be6
Source dataset
uspto-grants-1992_11
Patent number
US05162326

Reaction notes

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