Triethylamine → 4-Furan-2-yl-6-methylsulfanyl-5-phenylethynyl-pyrimidin-2-ylamine

HRID 1355826Notes

Reaction equation

HRID 1355826 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:11](I)=[C:10]([S:13][CH3:14])[N:9]=[C:8]([NH2:15])[N:7]=1.[C:16]1([C:22]#[CH:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>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.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:11]([C:23]#[C:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]([S:13][CH3:14])[N:9]=[C:8]([NH2:15])[N:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 185075894-Furan-2-yl-5-iodo-6-methylsulfanyl-pyrimidin-2-ylamine

Product 1

HCID 700037944-Furan-2-yl-6-methylsulfanyl-5-phenylethynyl-pyrimidin-2-ylamineYield 35%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

Following the method of Thorand and Krause (J. Org. Chem. 1998, 63, 8551), to a stirred solution of 500 mg (1.50 mmol) 4-furan-2-yl-5-iodo-6-methylsulfanyl-pyrimidin-2-ylamine in 10 ml dry degassed THF under argon at room temperature were added 211 mg (0.30 mmol) bis(triphenylphosphine)palladium(II) chloride, 10 mg (0.04 mmol) triphenylphosphine, 0.25 ml (2.28 mmol) phenylacetylene and 0.31 ml (2.22 mmol) triethylamine. Stirring was continued for 30 minutes then 3.0 mg (0.02 mmol) copper(I) iodide was added and the reaction mixture stirred for an additional 72 hours at room temperature. The reaction mixture was then concentrated in vacuo. Chromatography (1/4-1/1 ethyl acetate/hexane) afforded 161 mg (35%) 4-furan-2-yl-6-methylsulfanyl-5-phenylethynyl-pyrimidin-2-ylamine as a yellow crystalline solid. EI-MS m/e (%): 307 (M+, 100), 306 ([M—H]+, 52), 230 (38).

Workup

  1. customdegassed THF under argon at room temperature
  2. stirringthe reaction mixture stirred for an additional 72 hours at room temperature
  3. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-cc2f4c5d0a934585a24e1dc46e495769
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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