Triethylamine → HCID 44190037, compound

HRID 40540Notes

Reaction equation

HRID 40540 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[C:10]1([C:16]#[CH:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[CH3:9][S:8][C:5]1[N:4]=[CH:3][C:2]([C:17]#[C:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][N:6]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 11776TriphenylphosphineHCID 47385645-Bromo-2-(methylsulfanyl)pyrimidine

Product 1

HCID 44190037HCID 44190037, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Bis-(triphenylphosphine)-palladium(II)dichloride (120 mg, 0.16 mmol, 0.05 equiv.) were dissolved in 50 ml THF and 5-bromo-2-methylsulfanyl-pyrimidine (840 mg, 4.1 mmol) and phenylacetylene (410 μl, 4.1 mmol, 1 equiv.) were added at room temperature. Triethylamine (1.36 ml, 12.3 mmol, 3 equiv.), triphenylphosphine (28 mg, 0.12 mmol, 0.03 equiv.) and copper(I)iodide (19 mg, 0.08 mmol, 0.03 equiv.) were added and the mixture was stirred for 3 hours at 65° C. The reaction mixture was cooled and extracted once with saturated NaHCO3 solution and three times with ethyl acetate. The organic layers were combined, dried with sodium sulfate, filtered and evaporated to dryness. The crude product was purified by flash chromatography on silicagel (heptane:ethyl acetate 100:0->50:50). The desired 2-Methylsulfanyl-5-phenylethynyl-pyrimidine was obtained as a light yellow solid (400 mg, 44%), MS: m/e=227.3 (M+H+).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted once with saturated NaHCO3 solution and three times with ethyl acetate
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by flash chromatography on silicagel (heptane:ethyl acetate 100:0->50:50)

Sources & evidence

ORD record
ord-c1285cc3f48e45fcba3863c6b4ce2a19
Source dataset
uspto-grants-2013_09
Patent number
US08530472B2

Reaction notes

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