Water → HCID 70497128, compound

HRID 1429634Notes

Reaction equation

HRID 1429634 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:5]=[CH:6][C:7]([C:10]([O:12]C)=[O:11])=[N:8][CH:9]=1.O.O.[OH-].[Li+]>O1CCOCC1>[CH3:1][O:2][CH2:3][C:4]1[N:5]=[CH:6][C:7]([C:10]([OH:12])=[O:11])=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 168937Lithium hydroxide, monohydrateHCID 70498068HCID 70498068, compound

Product 1

HCID 70497128HCID 70497128, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 5-(methoxymethyl)pyrazine-2-carboxylate, 8-(1), (55 mg, crude) was dissolved in 1,4-dioxane (1 mL) and water (1 mL) was added followed by lithium hydroxide monohydrate (50 mg). After stirring at RT for 1 h, water (20 mL) was added and the mixture was extracted with ether (20 mL). The aqueous portion was acidified to pH 2 and extracted with EtOAc (2×25 mL). The combined EtOAc layers were dried over MgSO4 and evaporated to afford the title compound (19 mg). 1H NMR (400 MHz, CDCl3) δ ppm 3.58 (s, 3 H), 4.77 (s, 2 H), 8.80 (br. s., 1 H), 9.38 (br. s., 1 H)

Workup

  1. extractionthe mixture was extracted with ether (20 mL)
  2. extractionextracted with EtOAc (2×25 mL)
  3. dry with materialThe combined EtOAc layers were dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-0766d4d6b52c4d628a5647f519d8d526
Source dataset
uspto-grants-2015_01
Patent number
US08940734B2

Reaction notes

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