Water → HCID 68525809, compound

HRID 884178Notes

Reaction equation

HRID 884178 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][CH2:18][N:17]([CH2:21][C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=4)[C:16]3=[O:32])=[CH:11][C:10]=2[CH3:33])=[N:6][CH:7]=1.[C:34]([C:36]1[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=1)#[CH:35].C(N(CC)CC)C.O>CN1CCCC1=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.[Cu](I)I>[CH3:31][O:30][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][C:25]=1[O:28][CH3:29])[CH2:21][N:17]1[CH2:18][CH2:19][CH2:20][N:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][C:5]3[CH:4]=[CH:3][C:2]([C:35]#[C:34][C:36]4[CH:41]=[CH:40][C:39]([C:42]([F:43])([F:44])[F:45])=[CH:38][CH:37]=4)=[CH:7][N:6]=3)=[C:10]([CH3:33])[CH:11]=2)[C:16]1=[O:32]

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 43482951-Ethynyl-4-(trifluoromethyl)benzeneHCID 68527162HCID 68527162, compound

Product 1

HCID 68525809HCID 68525809, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of 1-[4-(5-bromopyridin-2-yloxy)-3-methylphenyl]-3-(3,4-dimethoxybenzyl)tetrahydropyrimidin-2-one (0.3 g, 0.59 mmol) in N-methylpyrrolidone (10 mL) were added bis(triphenylphosphine)palladium dichloride (20 mg, 0.03 mmol), copper iodide (11 mg, 0.059 mmol), 4-ethynyl-α,α,α-trifluorotoluene (0.14 mL, 0.88 mmol) and triethylamine (0.14 mL, 10 mmol) under a nitrogen atmosphere. The resulting solution was stirred for 3 hours at 110 to 120° C. After being left to cool, water was added to the reaction solution. The resulting solution was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was then evaporated, and the residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1→1:1), to thereby yield 0.28 g of the title compound.

Workup

  1. waitAfter being left
  2. temperatureto cool
  3. extractionThe resulting solution was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was then evaporated
  7. customthe residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1→1:1)

Sources & evidence

ORD record
ord-40005fa24cfb4d2994d26ed6e0c66156
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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