Diisopropylethylamine → 5-Furan-2-yl-pyrazin-2-ylamine

HRID 719984Notes

Reaction equation

HRID 719984 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5](Br)=[CH:4][N:3]=1.C(N(CC)C(C)C)(C)C.[Cl-].[Li+].C([Sn](CCCC)(CCCC)[C:25]1[O:26][CH:27]=[CH:28][CH:29]=1)CCC.[F-].[K+]>CN(C)C=O.C(Cl)Cl.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>[O:26]1[CH:27]=[CH:28][CH:29]=[C:25]1[C:5]1[N:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=1

Participants

9

Reactant 5

HCID 81531DiisopropylethylamineHCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 5995392-Amino-5-bromopyrazineHCID 43936882-(Tributylstannyl)furan

Product 1

HCID 218972055-Furan-2-yl-pyrazin-2-ylamineYield 77%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 2-amino-5-bromopyrazine (500 mg, 2.87 mmol) in N,N-dimethylformamide (15 mL) was treated with tetrakis(triphenylphosphine)palladium(0) (66 mg, 0.06 mmol), N,N-diisopropylethylamine (1.25 mL, 7.18 mmol), lithium chloride (426 mg, 10.06 mmol), and 2-(tributylstannyl)furan (905 μL, 2.87 mmol). The resulting reaction mixture was heated at 120° C. for 4 h. After such time, the reaction was cooled to 25° C., treated with a saturated aqueous potassium fluoride solution (10 mL), and then stirred at 25° C. overnight for 16 h. The solution was then diluted with methylene chloride (25 mL) and extracted with methylene chloride (3×15 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 98/2 to 96/4 methylene chloride/methanol) afforded 5-furan-2-yl-pyrazin-2-ylamine (356 mg, 77%) as a brown solid: mp 80.2–83.8° C.

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter such time, the reaction was cooled to 25° C.
  3. extractionextracted with methylene chloride (3×15 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8c629934fb63498da58aaaacb14f8266
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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