Ethyl orthoformate → 5-nitro-2-(1H-tetrazol-1-yl)pyridine

HRID 1502167Notes

Reaction equation

HRID 1502167 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH2:10])=[N:8][CH:9]=1)([O-:3])=[O:2].FC(F)(F)C(O[Si](C)(C)C)=O.[CH:22](OCC)(OCC)OCC.[N:32]([Si](C)(C)C)=[N+:33]=[N-:34]>CC(O)=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:22]=[N:32][N:33]=[N:34]2)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 31214Ethyl orthoformateHCID 67863Acetic acid, 2,2,2-trifluoro-, trimethylsilyl esterHCID 778882-Amino-5-nitropyridineHCID 78378Azidotrimethylsilane

Product 1

HCID 669272915-nitro-2-(1H-tetrazol-1-yl)pyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 5-nitropyridin-2-amine (1.00 g, 7.19 mmol) in AcOH was added trimethylsilyl trifluoroacetate (2.111 mL, 12.22 mmol). After stirring for 5 min, triethyl orthoformate (2.155 ml, 12.94 mmol) was added. Azidotrimethylsilane (1.513 mL, 11.50 mmol) was added after stirring for another 5 min. The reaction mixture was stirred at RT overnight, and was concentrated to give the crude solid. The solid was washed with DCM, and dried under vacuum to give title compound. LC/MS: [(M+1)]+=193.19, [(M+1-28)]+=165.19

Workup

  1. stirringafter stirring for another 5 min
  2. stirringThe reaction mixture was stirred at RT overnight
  3. concentrationwas concentrated
  4. customto give the crude solid
  5. washThe solid was washed with DCM
  6. customdried under vacuum

Sources & evidence

ORD record
ord-16ee0d2ec7524c22989cf557e60fff67
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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