Triethylamine → 5-Chloro-2-(trifluoromethyl)pyrimidine

HRID 852395

Reaction equation

HRID 852395 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([NH2:5])=[NH:4].[Cl:8]/[C:9](=[CH:14]\N(C)C)/[CH:10]=[N+](C)C.CCN1C2C(S/C/1=C\C#C/C(/C)=C\C1SC3C(=CC=CC=3)[N+]=1CC)=CC=CC=2.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C(#N)C.O>[Cl:8][C:9]1[CH:10]=[N:4][C:3]([C:2]([F:7])([F:6])[F:1])=[N:5][CH:14]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2776882TrifluoroacetamidineHCID 6477909Hexafluoro phosphateHCID 10590808HCID 10590808, compound

Product 1

HCID 336979605-Chloro-2-(trifluoromethyl)pyrimidineYield 56.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 4.70 g (85% purity, 35.65 mmol) of trifluoroacetamidine and 10.93 g (35.65 mmol) of ((Z)-2-chloro-3-dimethylamino-allylidene)-dimethyl-ammonium; hexafluoro phosphate [Davies, Ian W.; Marcoux, Jean-Francois; Wu, Jimmy; Palucki, Michael; Corley, Edward G.; Robbins, Michael A.; Tsou, Nancy, Ball, Richard G.; Dormer, Peter; Larsen, Robert D.; Reider, Paul J, Journal of Organic Chemistry 2000, 65(15), 4571-4574] in 70 ml acetonitrile was treated with 4.33 ml (42.78 mol) of triethylamine and stirred for 4 h at room temperature. The reaction was poured into 250 ml of water and extracted with ether (three times). The organic phases were washed with water (two times), dried (Na2SO4) and carefully evaporated to give 3.66 g of the title compound as an orange volatile liquid.

Workup

  1. extractionextracted with ether (three times)
  2. washThe organic phases were washed with water (two times)
  3. dry with materialdried (Na2SO4)
  4. customcarefully evaporated

Sources & evidence

ORD record
ord-7671513651e443afa296bc72042681e4
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Linked notes

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