2-(Trifluoromethyl)thiophene → 4-Chloro-6-methoxy-2-(5-trifluoromethyl-2-thienyl)pyrimidine

HRID 581811Notes

Reaction equation

HRID 581811 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1[S:4][CH:5]=[CH:6][CH:7]=1.C([Li])CCC.Cl[C:16]1[N:21]=[C:20]([Cl:22])[CH:19]=[C:18]([O:23][CH3:24])[N:17]=1>C(OCC)C.CCCCCC>[Cl:22][C:20]1[CH:19]=[C:18]([O:23][CH3:24])[N:17]=[C:16]([C:5]2[S:4][C:3]([C:2]([F:9])([F:8])[F:1])=[CH:7][CH:6]=2)[N:21]=1

Participants

6

Reactant 3

HCID 27607852-(Trifluoromethyl)thiopheneHCID 38245092,4-Dichloro-6-methoxypyrimidineHCID 178418339Butyllithium

Product 1

HCID 540993474-Chloro-6-methoxy-2-(5-trifluoromethyl-2-thienyl)pyrimidine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-40 °C

Procedure

2.05 g 2-Trifluoromethylthiophene in 20 mL diethylether are treated with 8.2 mL of a 1.6 M solution of n-butyllithium in hexane at -70° C. After 30 minutes the mixture is warmed to -40° C. and added dropwise to a solution of 2,4-dichloro-6-methoxypyrimidine in 20 mL of ether, which is kept at 0° C. The mixture is allowed to reach room temperature, is washed with water and 0.24 g of the product are isolated as an oil after flash chromatography.

Workup

  1. customis kept at 0° C
  2. customto reach room temperature
  3. washis washed with water and 0.24 g of the product
  4. customare isolated as an oil after flash chromatography

Sources & evidence

ORD record
ord-347e73111655408daa4eaa430869fbeb
Source dataset
uspto-grants-1999_07
Patent number
US05922726

Reaction notes

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