Sodium Chloride → HCID 21897211, compound

HRID 719943Notes

Reaction equation

HRID 719943 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[N:12][C:11]([O:14][CH2:15][CH:16]=[CH2:17])=[CH:10][N:9]=1)(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C(Cl)Cl>[CH2:15]([O:14][C:11]1[N:12]=[CH:13][C:8]([NH2:7])=[N:9][CH:10]=1)[CH:16]=[CH2:17]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67482615HCID 67482615, compound

Product 1

HCID 21897211HCID 21897211, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 5-allyloxy-pyrazin-2-yl-carbamic acid tert-butyl ester (400 mg, 1.59 mmol) in methylene chloride (2 mL) was treated with a 25% solution of trifluoroacetic acid in methylene chloride (5 mL). The mixture was stirred at 25° C. for 90 min, poured with stirring into a saturated aqueous sodium bicarbonate solution (50 mL) and then sodium chloride (3 g) was added. The resulting mixture was extracted with methylene chloride (3×25 mL), and each of the organic extracts was washed with a small portion of a saturated aqueous sodium chloride solution. The combined organic extracts were dried over potassium carbonate, filtered, and concentrated in vacuo to afford 5-allyloxy-pyrazin-2-ylamine (240 mg, 100%) as pale yellow crystals.

Workup

  1. additionpoured
  2. extractionThe resulting mixture was extracted with methylene chloride (3×25 mL)
  3. washeach of the organic extracts was washed with a small portion of a saturated aqueous sodium chloride solution
  4. dry with materialThe combined organic extracts were dried over potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-37b91868d15743648f8415d495a560b9
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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