Potassium Carbonate → 2-((3,5-dimethylisoxazol-4-yl)methyl)-2H-tetrazol-5-amine

HRID 1686319Notes

Reaction equation

HRID 1686319 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[NH2:6].Cl[CH2:8][C:9]1[C:10]([CH3:15])=[N:11][O:12][C:13]=1[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.ClCCl>[CH3:15][C:10]1[C:9]([CH2:8][N:2]2[N:3]=[N:4][C:5]([NH2:6])=[N:1]2)=[C:13]([CH3:14])[O:12][N:11]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 20467AminotetrazoleHCID 88246Isoxazole, 4-(chloromethyl)-3,5-dimethyl-

Product 1

HCID 574224592-((3,5-dimethylisoxazol-4-yl)methyl)-2H-tetrazol-5-amineYield 40%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2H-tetrazol-5-amine (1.29 g, 12.5 mmol), 4-(chloromethyl)-3,5-dimethylisoxazole (1.56 mL, 12.5 mmol) and potassium carbonate (1.73 g, 15.5 mmol) in DMF (20 mL) were heated to 80° C. with stirring for 16 hours. The reaction was cooled to room temperature, diluted with dichloromethane (100 mL) and washed consecutively with brine and water. The organics were dried over sodium sulfate and concentrated with rotary evaporation. The crude product was purified by silica gel chromatography (0-10% gradient ethyl acetate/dichloromethane) affording 2-((3,5-dimethylisoxazol-4-yl)methyl)-2H-tetrazol-5-amine as a white crystalline solid (970 mg, 40% yield) MS M+H calculated 195.1. found 195.

Workup

  1. washwashed consecutively with brine and water
  2. dry with materialThe organics were dried over sodium sulfate
  3. concentrationconcentrated with rotary evaporation
  4. customThe crude product was purified by silica gel chromatography (0-10% gradient ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-e7a9515f9cc746f29d06a375493a8d4d
Source dataset
uspto-grants-2012_04
Patent number
US08148544B2

Reaction notes

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