Triethylamine → HCID 44190037, compound

HRID 1942167Notes

Reaction equation

HRID 1942167 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) were dissolved in 50 ml THF and 5-bromo-2-methylsulfanyl-pyrimidine (840 mg, 4.1 mmol) and phenylacetylene (410 μl, 4.1 mmol) were added at room temperature. Triethylamine (1.36 ml, 12.3 mmol), triphenylphosphine (28 mg, 0.12 mmol) and copper(I)iodide (19 mg, 0.08 mmol) 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 compound 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-cfbd12d62157413abfcb27c295669fba
Source dataset
uspto-grants-2013_03
Patent number
US08389536B2

Reaction notes

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