Triethylamine → HCID 22599666, compound

HRID 1592279Notes

Reaction equation

HRID 1592279 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH3:9][C:10]([CH3:14])([CH3:13])[C:11]#[CH:12].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COC(C)(C)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)I.C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:12]#[C:11][C:10]([CH3:14])([CH3:13])[CH3:9])[N:5]=[CH:4][N:3]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 135123,3-Dimethyl-1-butyneHCID 709434,6-Dichloropyrimidine

Product 1

HCID 22599666HCID 22599666, compoundYield 47.8%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
45 °C

Procedure

Under an atmosphere of a nitrogen gas, 2.98 g of 4,6-dichloropyrimidine, 1.81 g of 3,3-dimethyl-1-butyne, 351 mg of dichlorobis(triphenylphosphine)palladium, 381 mg of copper iodide, 4.05 g of triethylamine and 525 mg of triphenylphosphine was added to 20 ml of acetonitrile and the suspension was stirred for 6 hours at 45° C. After cooling the reaction mixture was diluted with t-butyl methyl ether and washed three times with water. The organic layers were dried over sodium sulfate and concentrated. The residue was subjected to silica gel thin layer chromatography to give 1.86 g of 4-chloro-6-(3,3-dimethyl-1-butynyl)pyrimidine.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. washwashed three times with water
  3. dry with materialThe organic layers were dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-62e9883842c04021b6d1374f0db06015
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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