Potassium Carbonate → 4-[(4-Bromo-3,4,4-trifluorobutyl)thio]-6-(2,2,2-trifluoroethoxy)-pyrimidin

HRID 2292572Notes

Reaction equation

HRID 2292572 reaction equation
[F:1][C:2]([F:13])([F:12])[CH2:3][O:4][C:5]1[N:10]=[CH:9][NH:8][C:7](=[S:11])[CH:6]=1.Br[CH2:15][CH2:16][CH:17]([F:22])[C:18]([Br:21])([F:20])[F:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:21][C:18]([F:20])([F:19])[CH:17]([F:22])[CH2:16][CH2:15][S:11][C:7]1[CH:6]=[C:5]([O:4][CH2:3][C:2]([F:1])([F:12])[F:13])[N:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27834041,4-Dibromo-1,1,2-trifluorobutaneHCID 178506348HCID 178506348, compound

Product 1

HCID 214788724-[(4-Bromo-3,4,4-trifluorobutyl)thio]-6-(2,2,2-trifluoroethoxy)-pyrimidinYield 53.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

6-(2,2,2-trifluoroethoxy)-4(3H)-pyrimidinethione (see Example 1B) (3 g) and 1,4-dibromo-3,4,4-trifluorobutane (see Example 3A) (3.86 g) were added to acetone (50 cm3) containing potassium carbonate (1.97 g) and the mixture stirred at ambient temperature for 7 hours. After standing for a further 16 hours, tlc showed the reaction to be incomplete, so the mixture was heated to reflux for 5 hours. The reaction was then allowed to cool, inorganic solids were filtered off and washed with more acetone. Evaporation of the combined organic layers at reduced pressure afforded a brown oil which was chromatographed on silica gel, eluting with 1:4 ethyl acetate:hexane. This gave the title pyrimidine (3.05 g). M+ =399; 1H NMR (CDCl3): δ2.2-2.4(2H,m); 3.25-3.50(2H,m); 4.68-4.95(1H,m); 4.8(2H,q); 6.73(1H,s); 8.58(1H,s); (oil).

Workup

  1. waitAfter standing for a further 16 hours
  2. customthe reaction
  3. temperaturewas heated
  4. temperatureto reflux for 5 hours
  5. temperatureto cool
  6. filtrationinorganic solids were filtered off
  7. washwashed with more acetone
  8. customEvaporation of the combined organic layers at reduced pressure
  9. customafforded a brown oil which
  10. customwas chromatographed on silica gel
  11. washeluting with 1:4 ethyl acetate

Sources & evidence

ORD record
ord-7f9aa2d47cb6459ca91e32d4c1338689
Source dataset
uspto-grants-1997_11
Patent number
US05684011

Reaction notes

Loading…