Sodium Chloride → Methyl 5-morpholinopyrazine-2-carboxylate

HRID 639328Notes

Reaction equation

HRID 639328 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8](Cl)=[CH:7][N:6]=1)=[O:4].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.CCN(CC)CC.[Na+].[Cl-]>O1CCOCC1.O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:7][N:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 8083MorpholineHCID 8471TriethylamineHCID 406081Methyl 5-chloropyrazine-2-carboxylate

Product 1

HCID 52987628Methyl 5-morpholinopyrazine-2-carboxylateYield 90.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 4.9 g (28 mmol) 5-chloro-pyrazine-2-carboxylic acid methyl ester (commercially available), 3.2 g (37 mmol) morpholine and 7.37 g (73 mmol) NEt3 in 50 mL dioxane was heated to 45° C. for 16 h. Water and NaCl aq. was added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with NaCl aq., dried with MgSO4, filtered and evaporated. The residue was recrystallized from ethyl acetate to yield 5.65 g (89%) of the title compound as white solid. m/z (ES+): 224.3 (M+H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layers were washed with NaCl aq.
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c89e6a644aba40e78c1eada2dd145b29
Source dataset
uspto-grants-2010_04
Patent number
US07691863B2

Reaction notes

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