Ethyl orthoformate → tert-butyl [4-ethyl-6-(1H-tetrazol-1-yl)pyridin-3-yl]acetate

HRID 1502151Notes

Reaction equation

HRID 1502151 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[C:4]([CH2:16][CH3:17])[CH:3]=1.FC(F)(F)C(O[Si](C)(C)C)=O.[CH:29](OCC)(OCC)OCC.[N:39]([Si](C)(C)C)=[N+:40]=[N-:41]>CCOC(C)=O>[C:12]([O:11][C:9](=[O:10])[CH2:8][C:5]1[CH:6]=[N:7][C:2]([N:1]2[CH:29]=[N:39][N:40]=[N:41]2)=[CH:3][C:4]=1[CH2:16][CH3:17])([CH3:13])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 31214Ethyl orthoformateHCID 67863Acetic acid, 2,2,2-trifluoro-, trimethylsilyl esterHCID 78378AzidotrimethylsilaneHCID 131734298Tert-butyl (6-amino-4-ethylpyridin-3-yl)acetate

Product 1

HCID 125491612tert-butyl [4-ethyl-6-(1H-tetrazol-1-yl)pyridin-3-yl]acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (6-amino-4-ethylpyridin-3-yl)acetate (198 mg, 0.838 mmol) in EtOAc (4 mL) was added trimethylsilyl trifluoroacetate (0.246 ml, 1.424 mmol) at room temperature. After stirred 5 min, triethyl orthoformate (0.251 ml, 1.508 mmol) was added. After stirred another 5 min, azidotrimethylsilane (0.176 ml, 1.34 mmol) was added. The reaction mixture was stirred at RT for two days, then concentrated. The residue was purified prep TLC (hex/EA=1/1) to give title compound. LC-MS: [(M+1)]+=290.23, [(M+1-28)]+=262.22, [(M+1-28-56)]+=206.21

Workup

  1. stirringAfter stirred another 5 min
  2. stirringThe reaction mixture was stirred at RT for two days
  3. concentrationconcentrated
  4. customThe residue was purified prep TLC (hex/EA=1/1)

Sources & evidence

ORD record
ord-fb4fbedee28d4c1a8fb4f343a0cc5ee5
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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