Triethylamine → 1-Benzyl-5-chloro-3-(5-methyl-3-trimethylsilanylethynyl-pyridin-2-ylamino)-1H-pyrazin-2-one

HRID 1882202Notes

Reaction equation

HRID 1882202 reaction equation
[CH2:1]([N:8]1[CH:13]=[C:12]([Cl:14])[N:11]=[C:10]([NH:15][C:16]2[C:21](Br)=[CH:20][C:19]([CH3:23])=[CH:18][N:17]=2)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Si:32]([C:36]#[CH:37])([CH3:35])([CH3:34])[CH3:33]>C1COCC1.CCOC(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.[Cu](I)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([N:8]1[CH:13]=[C:12]([Cl:14])[N:11]=[C:10]([NH:15][C:16]2[C:21]([C:37]#[C:36][Si:32]([CH3:35])([CH3:34])[CH3:33])=[CH:20][C:19]([CH3:23])=[CH:18][N:17]=2)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 588801051-Benzyl-3-(3-bromo-5-methyl-pyridin-2-ylamino)-5-chloro-1H-pyrazin-2-one

Product 1

HCID 588800461-Benzyl-5-chloro-3-(5-methyl-3-trimethylsilanylethynyl-pyridin-2-ylamino)-1H-pyrazin-2-oneYield 96.5%

Reagents, catalysts & solvents 5

HCID 11776TriphenylphosphineCatalystHCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 26 (2.0 g, 4.9 mmol), triphenylphosphine (52 mg, 0.2 mmol), dichlorobis(triphenylphosphine)palladium(II) (173 mg, 0.25 mmol), triethylamine (1.03 mL, 7.4 mmol), and TMS-acetylene (1.05 mL, 7.4 mmol) were combined in THF (20 mL) at r.t. under nitrogen. After stirring 10 min, copper iodide (40 mg) was added, and the reaction stirred for 8 h. The reaction was diluted with EtOAc, washed with brine, dried (MgSO4), and concentrated in vacuo. Purification by silica gel chromatography (2:1:2 hexanes/EtOAc/CH2Cl2) gave 2.0 g (96%) of the title compound as a pale yellow solid. MS (ES) [m+H] calc'd for C21H23ClN4OSi, 423, 425; found 423, 425.

Workup

  1. stirringthe reaction stirred for 8 h
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography (2:1:2 hexanes/EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-034c2c5bc4304d2eba0ebf7e4fac16f7
Source dataset
uspto-grants-2012_11
Patent number
US08318939B2

Reaction notes

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