Nitrogen → 2-[2-(tert-Butyl-dimethyl-silanyloxymethyl)-oxazol-4-ylmethyl]-2H-[1,2,3]triazol-4-ylamine

HRID 42869Notes

Reaction equation

N#N.[C:3]([SiH2:7][O:8][C:9]([CH3:25])([CH3:24])[C:10]1[O:11][CH:12]=[C:13]([CH2:15][N:16]2[N:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[N:17]2)[N:14]=1)([CH3:6])([CH3:5])[CH3:4].[NH4+].[Cl-]>CCO.O.[Fe]>[C:3]([SiH2:7][O:8][C:9]([CH3:25])([CH3:24])[C:10]1[O:11][CH:12]=[C:13]([CH2:15][N:16]2[N:20]=[C:19]([NH2:21])[CH:18]=[N:17]2)[N:14]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

Conditions

Temperature: 75 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-[2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-4-ylmethyl]-4-nitro-2H-[1,2,3]triazole (103 mg, 0.30 mmol), iron powder (51 mg, 0.91 mmol) and NH4Cl (82 mg, 1.52 mmol) in a mixture of EtOH (3.0 mL) and water (1.5 mL) was stirred at 75° C. for 90 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. The residue was redissolved in CH2Cl2 (20 mL), dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a yellow oil. TLC:rf (19:1 CH2Cl2-MeOH)=0.20. LC-MS-conditions 02: tR=0.96 min; [M+H]+=310.46.

Workup

filtrationThe reaction mixture was filtered while hot and
concentrationconcentrated under reduced pressure
dissolutionThe residue was redissolved in CH2Cl2 (20 mL)
dry with materialdried over Na2SO4
filtrationfiltered
customthe solvents were removed under reduced pressure

Sources & evidence

ORD record: ord-f6cdf3c3543a4e1fa07a720d353f01a3
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536209B2

Reaction notes

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