Ethyl orthoformate → ethyl 2-(6-methyl-5-(1H-tetrazol-1-yl)pyridin-2-yl)acetate

HRID 1502126Notes

Reaction equation

HRID 1502126 reaction equation
FC(F)(F)C(O[Si](C)(C)C)=O.[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:17][C:18]=1[CH3:19].[CH:26](OCC)(OCC)OCC.[N:36]([Si](C)(C)C)=[N+:37]=[N-:38]>C(OCC)(=O)C.[Cl-].[Na+].O>[CH3:19][C:18]1[N:17]=[C:16]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:15]=[CH:14][C:13]=1[N:12]1[CH:26]=[N:36][N:37]=[N:38]1

Participants

7

Reactant 4

HCID 31214Ethyl orthoformateHCID 67863Acetic acid, 2,2,2-trifluoro-, trimethylsilyl esterHCID 78378AzidotrimethylsilaneHCID 89619013Ethyl 2-(5-amino-6-methyl-2-pyridinyl)acetate

Product 1

HCID 89618829ethyl 2-(6-methyl-5-(1H-tetrazol-1-yl)pyridin-2-yl)acetate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Trimethylsilyl trifluoroacetate (1.010 ml, 5.85 mmol) was added to a suspension of ethyl 2-(5-amino-6-methylpyridin-2-yl)acetate (710 mg, 3.66 mmol) in ethyl acetate (20 ml). The mixture was stirred for 5 mins then added triethyl orthoformate (1.096 ml, 6.58 mmol). Stirred for another 5 mins then added azidotrimethylsilane (0.817 ml, 6.21 mmol). The reaction was stirred overnight. The reaction was poured into brine and extracted with ethyl acetate. The ethyl acetate was separated, dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography through 120 g ISCO Redi-Sep column and eluted with 5% MeOH/DCM to yield ethyl 2-(6-methyl-5-(1H-tetrazol-1-yl)pyridin-2-yl)acetate.

Workup

  1. stirringStirred for another 5 mins
  2. stirringThe reaction was stirred overnight
  3. extractionextracted with ethyl acetate
  4. customThe ethyl acetate was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography through 120 g ISCO Redi-Sep column
  9. washeluted with 5% MeOH/DCM

Sources & evidence

ORD record
ord-c17893495e894d6ebfcf882a70a1d28d
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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