Dimethylformamide → 3,6-diethyl-N-(1-ethylpropyl)-5-(5,6,7,8-tetrahydronaphthalen-2-yl)pyrazin-2-amine

HRID 1063259Notes

Reaction equation

HRID 1063259 reaction equation
FC(F)(F)S(O[C:7]1[C:16]([C:17]2[C:22]([CH2:23][CH3:24])=[N:21][C:20]([NH:25][CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[C:19]([CH2:31][CH3:32])[N:18]=2)=[CH:15][C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=1)(=O)=O.CN(C=O)C.C([SiH](CC)CC)C>C(OCC)(=O)C.O.C1(PCCCPC2C=CC=CC=2)C=CC=CC=1>[CH2:31]([C:19]1[C:20]([NH:25][CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[N:21][C:22]([CH2:23][CH3:24])=[C:17]([C:16]2[CH:7]=[CH:8][C:9]3[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=3[CH:15]=2)[N:18]=1)[CH3:32]

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 12052TriethylsilaneHCID 222786903-{3,6-Diethyl-5-[(1-ethylpropyl)amino]pyrazin-2-yl}-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

Product 1

HCID 222787203,6-diethyl-N-(1-ethylpropyl)-5-(5,6,7,8-tetrahydronaphthalen-2-yl)pyrazin-2-amineYield 76%

Reagents, catalysts & solvents 3

HCID 43668911,3-Bis(phenylphosphino)propaneCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A 7 mL oven dried vial was charged with 3-{3,6-diethyl-5-[(1-ethylpropyl)amino]pyrazin-2-yl}-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (100 mg 0.2 mmol), 1,3-diphenylphosphinopropane (1.65 mg, 0.004 mmol), Pd(AcO)2 (0.9 mg, 0.004 mmol), and DMF (0.5 mL). The reaction was heated to 60° C. on the orbital shaker. Triethyl silane (0.08 mL, 0.5 mmol) was added at once. A color change from yellow to dark orange was observed. The vial was re-sealed with a teflon lined cap and heated to 60° C. for 2 hours. After cooling to ambient temperature, the reaction was diluted with ethyl acetate, poured in H2O, washed once with sat. aq. NaHCO3 and once with Brine. The organic layer was dried with Na2SO4, filtered and concentrated to 120 mg of a crude oil. The crude was purified by Biotage MPLC (40 g column, toluene) to give 53 mg (76%) of 3,6-diethyl-N-(1-ethylpropyl)-5-(5,6,7,8-tetrahydronaphthalen-2-yl)pyrazin-2-amine as a clear oil. Rf 0.18 (toluene). IR (liq.) 2964, 2933, 2874, 2858, 2837, 1558, 1508, 1483, 1463, 1444, 1392, 1381, 1212, 1173, 833 cm−1. OAMS supporting ions at: ESI+352.2. Anal. Calcd for C23H33N3: C, 78.58; H, 9.46; N, 11.95. Found: C, 78.20; H, 9.25; N, 11.95.

Workup

  1. customA 7 mL oven dried vial
  2. customlined cap
  3. temperatureheated to 60° C. for 2 hours
  4. temperatureAfter cooling to ambient temperature
  5. washwashed once with sat. aq. NaHCO3 and once with Brine
  6. dry with materialThe organic layer was dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to 120 mg of a crude oil
  9. customThe crude was purified by Biotage MPLC (40 g column, toluene)

Sources & evidence

ORD record
ord-7517a9cb383744ddb7658176e4c76b06
Source dataset
uspto-grants-2005_11
Patent number
US06964965B2

Reaction notes

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