Ethyl orthoformate → ethyl [5-(1H-tetrazol-1-yl)pyrazin-2-yl]acetate

HRID 2173331Notes

Reaction equation

HRID 2173331 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:6][CH:7]=1.[CH:14](OCC)(OCC)OCC.[N-:24]=[N+:25]=[N-:26].[Na+]>CC(O)=O>[N:1]1([C:2]2[N:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[N:6][CH:7]=2)[CH:14]=[N:26][N:25]=[N:24]1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 72212710Ethyl 2-(5-aminopyrazin-2-YL)acetate

Product 1

HCID 77230648ethyl [5-(1H-tetrazol-1-yl)pyrazin-2-yl]acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of the ethyl (5-aminopyrazin-2-yl)acetate (2.0 g, 11.0 mmol) and triethyl orthoformate (4.9 g, 33.1 mmol) in 60 mL of HOAc was added sodium azide (0.9 g, 13.8 mmol) and heated to 100° C. for 1 hour. The reaction was completed which was checked by TLC. The reaction mixture was cooled to r.t. The solvent was removed under vacuum. The residue was dissolved in EtOAc, washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatograph to afford the product ethyl [5-(1H-tetrazol-1-yl)pyrazin-2-yl]acetate. 1H-NMR (400 MHz, CDCl3) δ ppm 9.50 (s, 1H), 9.35 (s, 1H), 8.54 (s, 1H), 4.21 (q, J=7.2 Hz, 2H), 3.98 (s, 2H), 1.27 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to r.t
  2. customThe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatograph

Sources & evidence

ORD record
ord-cc417bf4702c443c9250bd76e81d6441
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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