Chloropyrazine → HCID 117702448, compound

HRID 1503265Notes

Reaction equation

HRID 1503265 reaction equation
[C:1]([C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][C:5]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])([CH2:6]3)[CH2:4]1)[CH2:10]2)#[CH:2].Cl[C:22]1[CH:27]=[N:26][CH:25]=[CH:24][N:23]=1>C(#N)C.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:23]1[CH:24]=[CH:25][N:26]=[CH:27][C:22]=1[C:2]#[C:1][C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][C:5]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])([CH2:6]3)[CH2:4]1)[CH2:10]2

Participants

6

Reactant 2

HCID 73277ChloropyrazineHCID 117702591HCID 117702591, compound

Product 1

HCID 117702448HCID 117702448, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of tert-butyl 3-ethynyl-1-adamantylcarbamate (120 mg, 0.44 mmol) and 2-chloropyrazine (120 mg, 1.05 mmol) in TEA (3 mL) and acetonitrile (15 mL) was added Pd(PPh3)4 (5 mg, 0.04 mmol), followed by an addition of Cut (5 mg, 0.026 mmol) under N2 atmosphere. After stirring at 70° C. for three hours, the reaction was cooled to room temperature, diluted with ethyl acetate (50 mL), washed with water (50 mL) and brine, dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5/1) to give 108 mg (70%) of the title compound, tert-butyl 3-(pyrazin-2-ylethynyl)-1-adamantylcarbamate as a white solid. ESI-MS m/z: 298 (M-55)+.

Workup

  1. additionfollowed by an addition of Cut (5 mg, 0.026 mmol) under N2 atmosphere
  2. temperaturethe reaction was cooled to room temperature
  3. washwashed with water (50 mL) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-3df4743fe32e4977aa916957f09f6ad7
Source dataset
uspto-grants-2015_12
Patent number
US09212165B2

Reaction notes

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