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

HRID 32773

Reaction equation

HRID 32773 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([NH2:5])=[NH:4].F[P-](F)(F)(F)(F)F.[Cl:15]/[C:16](=[CH:21]\N(C)C)/[CH:17]=[N+](C)C.C(N(CC)CC)C>C(#N)C>[Cl:15][C:16]1[CH:17]=[N:4][C:3]([C:2]([F:7])([F:6])[F:1])=[N:5][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2776882TrifluoroacetamidineHCID 105908072-Chloro-1,3-bis(dimethylamino)trimethinium hexafluorophosphate

Product 1

HCID 336979605-Chloro-2-(trifluoromethyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 38 mmol trifluoroacetamidine in 70 ml acetonitrile was added 37.92 mmol ((Z)-2-Chloro-3-dimethylamino-allylidene)-dimethyl-ammonium hexafluoro phosphate (CAS: 291756-76-8) followed by 45.5 mmol triethylamine. The yellow solution was stirred at room temperature for 5 hours, then poured onto water and extracted 3 times with ether. The combined extracts were dried over sodium sulfate, filtered and distilled at 760 mm Hg to provide the title compound. MS (m/e): 182.2 (M+, 100%)

Workup

  1. additionpoured onto water
  2. extractionextracted 3 times with ether
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. distillationdistilled at 760 mm Hg

Sources & evidence

ORD record
ord-71874eeb6848488aa5302314746074db
Source dataset
uspto-grants-2008_09
Patent number
US07427612B2

Linked notes

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