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

HRID 2065087Notes

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[CH: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[CH: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-(tert-butyl-dimethyl-silanyloxymethyl)-4-(4-nitro-pyrazol-1-ylmethyl)-oxazole (408 mg, 1.20 mmol), iron powder (204 mg, 3.62 mmol) and NH4Cl (326 mg, 6.03 mmol) in a mixture of EtOH (6.0 mL) and water (3.0 mL) was stirred at 75° C. for 45 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 an orange oil. TLC: rf (EA)=0.20. LC-MS-conditions 02: tR=0.81 min; [M+H]+=309.07.

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-a4300776faaa4781a23178ff48852e5b
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288419B2

Reaction notes

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