Triethylamine → HCID 18446621, compound

HRID 1269048Notes

Reaction equation

HRID 1269048 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([F:8])[CH:3]=1.C(N(CC)CC)C.[C:16]([C:18]1[CH:23]=[CH:22][N:21]=[C:20]([S:24][CH3:25])[N:19]=1)#[CH:17]>O1CCCC1.[Cu]I>[F:8][C:4]1[CH:3]=[C:2]([C:17]#[C:16][C:18]2[CH:23]=[CH:22][N:21]=[C:20]([S:24][CH3:25])[N:19]=2)[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 70235702-Fluoro-4-iodopyridineHCID 179654774-Ethynyl-2-(methylthio)pyrimidine

Product 1

HCID 18446621HCID 18446621, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

4-Iodo-2-fluoropyridine (1.09 g, 4.9 mmol) was dissolved in anhydrous tetrahydrofuran (20 mL). To this solution was added triethylamine (0.9 mL, 6.5 mmol), copper (I) iodide (80 mg, 0.4 mmol) and dichlorobis(triphenylphosphine) palladium (II) (60 mg, 0.32 mmol). 4-Ethynyl-2-(methylsulfanyl)pyrimidine (example 4, 0.75 g, 4.9 mmol) in tetrahydrofuran was added dropwise to the resulting solution. After the addition was complete the reaction was stirred at room temperature overnight. The mixture was concentrated to give a syrup, that was purified by silica gel chromatography (1:1 ethyl acetate:hexane) to give after removal of solvents 0.84 g (70%) of 4-[(2-fluoro-4-pyridinyl)ethynyl]-2-(methylsulfanyl)pyrimidine as a white solid. 1H NMR (CDCl3): δ 8.61 (d, 1H), 8.32 (d, 1H), 7.39 (d, 1H), 7.17 (m, 2H), 2.64 (s, 3H); 19F NMR (CDCl3): 8–66.82; MS m/z 246 (M+1).

Workup

  1. additionAfter the addition
  2. concentrationThe mixture was concentrated
  3. customto give a syrup, that
  4. customwas purified by silica gel chromatography (1:1 ethyl acetate:hexane)
  5. customto give
  6. customafter removal of solvents 0.84 g (70%) of 4-[(2-fluoro-4-pyridinyl)ethynyl]-2-(methylsulfanyl)pyrimidine as a white solid

Sources & evidence

ORD record
ord-6c275077787044279039e66c2dc11459
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

Loading…