Sodium Azide → 4-azido-5,6-diphenyl-2-(trifluoromethyl)pyrimidine

HRID 2250330Notes

Reaction equation

HRID 2250330 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:5]=[C:4]([C:20]([F:23])([F:22])[F:21])[N:3]=1.[N-:24]=[N+:25]=[N-:26].[Na+]>C(O)C>[N:24]([C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:5]=[C:4]([C:20]([F:23])([F:22])[F:21])[N:3]=1)=[N+:25]=[N-:26]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 104046804-Chloro-5,6-diphenyl-2-(trifluoromethyl)pyrimidine

Product 1

HCID 102466744-azido-5,6-diphenyl-2-(trifluoromethyl)pyrimidineYield 88.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloro-5,6-diphenyl-2-(trifluoromethyl)pyrimidine (0.5 g, 1.5 mmol) (synthesized according to the procedure described in example 1) was refluxed in ethanol (10 ml) containing sodium azide (0.1 g, 1.5 mmol) for 8 hours and allowed to cool to room temperature. The reaction mixture was poured onto ice-water mixture. The solid thus separated was extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the title compound (0.45 g, 88.3%, HPLC purity 98.5%), mp: 126-128° C.

Workup

  1. additionThe reaction mixture was poured onto ice-water mixture
  2. customThe solid thus separated
  3. extractionwas extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bf99aac1318e476996a3fb0256370cac
Source dataset
uspto-grants-2008_01
Patent number
US07317014B2

Reaction notes

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