Sodium Azide → 4-[4-(3-Azidopropyl)piperazin-1-yl]-2-tert-butyl-6-(trifluoromethyl)pyrimidine

HRID 1678074Notes

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([C:9]1[N:14]=[C:13]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23]Cl)[CH2:17][CH2:16]2)[CH:12]=[C:11]([C:25]([F:28])([F:27])[F:26])[N:10]=1)([CH3:8])([CH3:7])[CH3:6]>CN(C)C=O.[Cl-].[Na+].O>[N:1]([CH2:23][CH2:22][CH2:21][N:18]1[CH2:17][CH2:16][N:15]([C:13]2[CH:12]=[C:11]([C:25]([F:27])([F:28])[F:26])[N:10]=[C:9]([C:5]([CH3:6])([CH3:8])[CH3:7])[N:14]=2)[CH2:20][CH2:19]1)=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 70 °C

Procedure

2.4 g (36.9 mmol) of sodium azide were added to 13.5 g (36.9 mmol) of 2-tert-butyl-4-[4-(3-chloropropyl)piperazin-1-yl]-6-(trifluoromethyl)pyrimidine (DE 197 35 410) in 60 ml of N,N-dimethylformamide (DMF), and the mixture was stirred at 70° C. for 3 hours. The reaction mixture was allowed to cool to room temperature, the mixture was poured into saturated brine, and the aqueous mixture was extracted with ethyl acetate. The organic phase was washed three times with an NaCl solution, dried over Na2SO4, filtered to remove the desiccant and concentrated in vacuo. Yield: 13.7 g.

Workup

temperatureto cool to room temperature
extractionthe aqueous mixture was extracted with ethyl acetate
washThe organic phase was washed three times with an NaCl solution
dry with materialdried over Na2SO4
filtrationfiltered
customto remove the desiccant and
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3cbcbb8643bc41329aeadf9c55070a7a
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008488B2

Reaction notes

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