Ethyl orthoformate → methyl 2-(4-methyl-5-(1H-tetrazol-1-yl)pyridin-2-yl)acetate

HRID 1502123Notes

Reaction equation

HRID 1502123 reaction equation
[NH2:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[N:6][CH:7]=1.[CH:14](OCC)(OCC)OCC.[N-:24]=[N+:25]=[N-:26].[Na+]>C(O)(=O)C.[Cl-].[Na+].O>[CH3:13][C:3]1[C:2]([N:1]2[CH:14]=[N:26][N:25]=[N:24]2)=[CH:7][N:6]=[C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:4]=1

Participants

6

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 89619043Methyl 2-(5-amino-4-methyl-2-pyridinyl)acetate

Product 1

HCID 89619214methyl 2-(4-methyl-5-(1H-tetrazol-1-yl)pyridin-2-yl)acetate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 2-(5-amino-4-methylpyridin-2-yl)acetate (90 mg, 0.499 mmol) was stirred in acetic acid (3 ml) then added triethyl orthoformate (0.166 ml, 0.999 mmol) and sodium azide (58.4 mg, 0.899 mmol). The mixture was stirred at 80° C. for 3 hrs then diluted with brine and extracted with ethyl acetate. The organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue was chromatographed thru 40 g ISCO Redi-sep column and eluted with 5% MeOH/DCM to yield methyl 2-(4-methyl-5-(1H-tetrazol-1-yl)pyridin-2-yl)acetate: 1H-NMR (500 MHz, CDCl3) δ ppm 8.867 (s, 1H), 8.527 (s, 1H), 7.438 (s, 1H), 3.963 (s, 2H), 3.790 (s, 3H), 2.308 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was chromatographed
  6. washeluted with 5% MeOH/DCM

Sources & evidence

ORD record
ord-68345b8e318f4292a36cba76f16918c7
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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