Triethylamine → HCID 18446615, compound

HRID 1269038Notes

Reaction equation

HRID 1269038 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.C(N(CC)CC)C.[C:17]([C:19]1[CH:24]=[CH:23][N:22]=[C:21]([S:25][CH3:26])[N:20]=1)#[CH:18].C(OCC)(=O)C>O1CCCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH3:9][S:8][C:4]1[N:3]=[C:2]([C:18]#[C:17][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([S:25][CH3:26])[N:20]=2)[CH:7]=[CH:6][N:5]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 38589014-Iodo-2-(methylthio)pyrimidineHCID 179654774-Ethynyl-2-(methylthio)pyrimidine

Product 1

HCID 18446615HCID 18446615, compoundYield 69.3%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

4-Iodo-2-(methylsulfanyl)pyrimidine (1.76 g, 7.1 mmol) was dissolved in anhydrous tetrahydrofuran (50 mL). To this solution was added triethylamine (1.2 mL, 8.5 mmol), copper (I) iodide (70 mg, 0.4 mmol) and dichlorobis(triphenylphosphine)palladium (II) (150 mg, 0.21 mmol). A solution of 4-ethynyl-2-(methylsulfanyl)pyrimidine (1.0 g, 7.1 mmol) in tetrahydrofuran was added dropwise. The reaction mixture was stirred at room temperature overnight Ethyl acetate and water were added to the reaction mixture. The phases were separated and the aqueous phase extracted with additional ethyl acetate. The organics were combined, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (1:1 ethyl acetate:hexane) gave 1.35 g (69%) of 2-(methylsulfanyl)-4-{[2-(methylsulfanyl)-4-pyrimidinyl]ethynyl}pyrimidine as a white solid. 1H NMR (CDCl3): δ 8.57 (d, 2H), 7.19 (d, 2H), 2.59 (s, 6H); MS m/z 275 (M+1).

Workup

  1. additionwere added to the reaction mixture
  2. customThe phases were separated
  3. extractionthe aqueous phase extracted with additional ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (1:1 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-d4bfed710d944fa788e1feb3f9d5eaa1
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

Loading…