Ethyl orthoformate → tert-butyl[2-(1H-tetrazol-1-yl)pyrimidin-5-yl]acetate

HRID 1502148Notes

Reaction equation

HRID 1502148 reaction equation
FC(F)(F)C(O[Si](C)(C)C)=O.[NH2:12][C:13]1[N:18]=[CH:17][C:16]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:15][N:14]=1.[CH:27](OCC)(OCC)OCC.[N:37]([Si](C)(C)C)=[N+:38]=[N-:39]>C(OCC)(=O)C>[C:23]([O:22][C:20](=[O:21])[CH2:19][C:16]1[CH:15]=[N:14][C:13]([N:12]2[CH:27]=[N:37][N:38]=[N:39]2)=[N:18][CH:17]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 31214Ethyl orthoformateHCID 67863Acetic acid, 2,2,2-trifluoro-, trimethylsilyl esterHCID 78378AzidotrimethylsilaneHCID 89762649Tert-butyl (2-aminopyrimidin-5-yl)acetate

Product 1

HCID 131734297tert-butyl[2-(1H-tetrazol-1-yl)pyrimidin-5-yl]acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Trimethylsilyl trifluoroacetate (0.14 mL, 0.81 mmol) was added to a suspension of tert-butyl (2-aminopyrimidin-5-yl)acetate (100 mg, 0.478 mmol) in Ethyl acetate (1.5 mL). The reaction mixture was stirred at RT for 5 minutes and triethyl orthoformate (0.14 mL, 0.84 mmol) was added. The reaction mixture was stirred at RT for 5 minutes and azidotrimethylsilane (0.1 mL, 0.760 mmol) was added. The reaction mixture was stirred at RT overnight. The reaction mixture was diluted with EtOAc and washed with water and brine, dried (MgSO4), filtered and the solvent evaporated to afford the title compound: LC/MS (M+1)+ at 263 and (M+1-N2-tBu)+ at 179.

Workup

  1. stirringThe reaction mixture was stirred at RT for 5 minutes
  2. stirringThe reaction mixture was stirred at RT overnight
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-d9e8498d6fab48c2aa2181251e1a16f6
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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