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

HRID 349179Notes

Reaction equation

HRID 349179 reaction equation
[CH3:1][O-:2].[Na+].CC[CH:6]([NH:9][C:10]1[CH:15]=[N:14][CH:13]=[C:12](Cl)[N:11]=1)[CH2:7]C.CN1[CH2:22][CH2:21][CH2:20]C1=O>CO>[CH2:6]([NH:9][C:10]1[C:15]([CH2:20][CH2:21][CH3:22])=[N:14][CH:13]=[C:12]([O:2][CH3:1])[N:11]=1)[CH3:7]

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

A solution of sodium methoxide in methanol (5.0M, 10 ml) I s added to a solution of 2-(3-pentylamino)-6-chloropyrazine (3.3 g, 16.5 mmol) in 1-methyl-2-pyrrolidinone (15 mL) at room temperature. The resulting solution is heated to 50° C. for 20 hours then evaporated and poured into water and extracted twice with ethyl acetate/hexane (1:1). Combined extracts are 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 are dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed

Sources & evidence

ORD record
ord-85c82cac19094bc18c2b4be37007dfcb
Source dataset
uspto-grants-2007_02
Patent number
US07179807B2

Reaction notes

Loading…