Triethylamine → HCID 23498911, compound

HRID 1836880Notes

Reaction equation

HRID 1836880 reaction equation
[C:1]([C:3]1[C:4]([CH:17]=[O:18])=[CH:5][C:6]2[C:7]([CH3:16])([CH3:15])[CH2:8][CH2:9][C:10]([CH3:14])([CH3:13])[C:11]=2[CH:12]=1)#[CH:2].Br[C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1.C(N(CC)CC)C>CN(C)C=O.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>[CH3:14][C:10]1([CH3:13])[CH2:9][CH2:8][C:7]([CH3:16])([CH3:15])[C:6]2[CH:5]=[C:4]([CH:17]=[O:18])[C:3]([C:1]#[C:2][C:20]3[N:25]=[CH:24][CH:23]=[CH:22][N:21]=3)=[CH:12][C:11]1=2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 783452-BromopyrimidineHCID 234989213-Ethynyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaldehyde

Product 1

HCID 23498911HCID 23498911, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 0.400 g (1.66 mmol) of 3-ethynyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthaldehyde, 0.278 g (1.75 mmol) of 2-bromopyrimidine, 0.053 g (0.075 mmol) of dichlorobis(triphenylphosphine)palladium(II), 0.026 g (0.14 mmol) of cuprous iodide, and 0.253 g (2.50 mmol) of triethylamine in 12 mL of dimethylformamide was heated to 45° C. for 3 hours, cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The product was purified by flash chromatography on silica gel (25% ethyl acetate/hexane) to afford 0.372 g (70%) of 5,5,8,8-tetramethyl-3-pyrimidin-2-ylethynyl-5,6,7,8-tetrahydro-2-naphthaldehyde.(M+=318).

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by flash chromatography on silica gel (25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-597b57be71ac42c2b994c04773670cca
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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