Triethylamine → HCID 69782266, compound

HRID 1355811Notes

Reaction equation

HRID 1355811 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]#[N:10])=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1.[C:17]1([C:23]#[CH:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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>[NH2:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:5]([C:9]#[N:10])=[C:6]([C:24]#[C:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 18507370HCID 18507370, compound

Product 1

HCID 69782266HCID 69782266, compoundYield 55%

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 (2.17 mmol) 2-amino-4-chloro-6-phenyl-pyrimidine-5-carbonitrile in 8.5 ml dry degassed THF under argon at room temperature were added 300 mg (0.43 mmol) bis(triphenylphosphine)palladium(II) chloride, 14 mg (0.05 mmol) triphenylphosphine, 0.36 ml (3.28 mmol) phenylacetylene and 0.45 ml (3.23 mmol) triethylamine. Stirring was continued for 30 minutes then 4.0 mg (0.02 mmol) copper(I) iodide was added and the reaction mixture stirred for an additional 16 hours at room temperature. The reaction mixture was then concentrated in vacuo. Chromatography (1/2 ethyl acetate/hexane) afforded 350 mg (55%) 2-amino-4-phenyl-6-phenylethynyl-pyrimidine-5-carbonitrile as a light yellow crystalline solid. EI-MS m/e (%): 296 (M+, 100), 270 (80).

Workup

  1. customdegassed THF under argon at room temperature
  2. stirringthe reaction mixture stirred for an additional 16 hours at room temperature
  3. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-8e54e624b27a444f821dca54b1d17a01
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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