N-methyl-2-pyrrolidone → HCID 69433518, compound

HRID 1270326Notes

Reaction equation

HRID 1270326 reaction equation
CC[CH:3]([NH:6][C:7]1[CH:12]=[N:11][CH:10]=[C:9](Cl)[N:8]=1)[CH2:4]C.[CH3:14][O-:15].[Na+].CN1[CH2:22][CH2:21][CH2:20]C1=O>CO>[CH2:3]([NH:6][C:7]1[C:12]([CH2:20][CH2:21][CH3:22])=[N:11][CH:10]=[C:9]([O:15][CH3:14])[N:8]=1)[CH3:4]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 10942334Sodium MethoxideHCID 22249036HCID 22249036, compound

Product 1

HCID 69433518HCID 69433518, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(3-pentylamino)-6-chloropyrazine (3.3 g, 16.5 mmol) (obtained in example 75) in 1-methyl-2-pyrrolidinone (15 mL) at room temperature is added a solution of sodium methoxide in methanol (5.0M, 10 ml). The resulting solution was heated to 50° C. for 20 h then evaporated and poured into water and extracted twice with ethyl acetate/hexane (1:1). Combined extracts were dried (sodium sulfate), filtered, concentrated, and chromatographed to give N-(1-ethyl)propyl-6-methoxypyrazine-2-amine as a light yellow solid(98%).

Workup

  1. customthen evaporated
  2. additionpoured into water
  3. extractionextracted twice with ethyl acetate/hexane (1:1)
  4. dry with materialCombined extracts were dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed

Sources & evidence

ORD record
ord-22f892c4adf042f68108f92b35f3ddbe
Source dataset
uspto-grants-2007_04
Patent number
US07202250B2

Reaction notes

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