N,N'-Dimethylethylenediamine → HCID 25169201, compound

HRID 906242Notes

Reaction equation

HRID 906242 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][S:9][C:10]1[C:11](=[O:16])[NH:12][CH:13]=[CH:14][N:15]=1.Br[C:18]1[CH:29]=[CH:28][C:21]([O:22][CH2:23][C:24]([CH3:27])([OH:26])[CH3:25])=[C:20]([CH3:30])[CH:19]=1.CNCCNC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[OH:26][C:24]([CH3:27])([CH3:25])[CH2:23][O:22][C:21]1[CH:28]=[CH:29][C:18]([N:12]2[CH:13]=[CH:14][N:15]=[C:10]([S:9][CH2:8][CH2:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[C:11]2=[O:16])=[CH:19][C:20]=1[CH3:30]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 57540533HCID 57540533, compoundHCID 57540608HCID 57540608, compound

Product 1

HCID 25169201HCID 25169201, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 3-(2-(pyridin-2-yl)ethylthio)pyrazin-2(1H)-one (100 mg, 0.429 mmol), which was prepared by the procedure described in Method 7 except for substitution of 2-(2-pyridylethylthiol) for 2-(4-chlorophenethanol), 1-(4-bromo-2-methylphenoxy)-2-methylpropan-2-ol (133 mg, 0.514 mmol), N1,N2-dimethylethane-1,2-diamine (113 mg, 1.286 mmol), K3PO4 (0.106 mL, 1.286 mmol) and copper(1) iodide (82 mg, 0.429 mmol) in dioxane (1.0 mL) was stirred at 115° C. for 90 min. The reaction mixture, after cooling to RT, was filtered and the filtrate was concentrated. The crude product was purified by silica gel chromatography employing a solvent gradient (hexane to 100% ethyl acetate) to yield 1-(4-(2-hydroxy-2-methylpropoxy)-3-methylphenyl)-3-(2-(pyridin-2-yl)ethylthio)pyrazin-2(1H)-one (140 mg, 0.340 mmol, 79% yield) as white solid. MS (M+H 412). 1H NMR (400 MHz, MeOD) δ ppm 8.67 (1H, d), 8.48 (1H, td, J=7.91, 1.51 Hz), 8.02 (1H, d, J=8.28 Hz), 7.81-7.95 (1H, m), 7.07-7.29 (4H, m), 6.93 (1H, d, J=8.78 Hz), 3.76 (2H, s), 3.35-3.57 (4H, m), 2.22 (3H, s), 1.27 (6H, s).

Workup

  1. customwas prepared by the procedure
  2. temperatureThe reaction mixture, after cooling to RT
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1374720d15c24bef85d9489dde2a4f85
Source dataset
uspto-grants-2011_09
Patent number
US08012984B2

Reaction notes

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