Tetrahydrofuran → HCID 118046270, compound

HRID 595875Notes

Reaction equation

HRID 595875 reaction equation
I[C:2]1[N:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[C:9]([O:13][CH3:14])(=[O:12])[C:10]#[CH:11].C(=O)([O-])[O-].[K+].[K+].C1COCC1>O.[Cu]I>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:11]#[C:10][C:9]([O:13][CH3:14])=[O:12])=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 13536Methyl propiolateHCID 206255785-Iodopyrazin-2-amine

Product 1

HCID 118046270HCID 118046270, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a 5 mL of microwave vial was added 5-iodopyrazin-2-amine (100 mg, 0.452 mmol), methyl propiolate (161 μL, 1.810 mmol), potassium carbonate (125 mg, 0.905 mmol), copper (I) iodide (3.45 mg, 0.018 mmol), and THF (1508 μL). The reaction mixture was heated at 65° C. for 2 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo. The crude product was purified by flash chromatography (20% EtOAc in DCM) yielding methyl 3-(5-aminopyrazin-2-yl)propiolate (38%). LCMS (m/z): 178.4 (MH+), 0.48 min.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe crude product was purified by flash chromatography (20% EtOAc in DCM)

Sources & evidence

ORD record
ord-e8e8065f1e864a189562e29927d35337
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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