Tetrahydrofuran → HCID 21548009, compound

HRID 2079979Notes

Reaction equation

HRID 2079979 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[C:13]([NH2:14])=[N:12][C:11]([NH2:15])=[CH:10][N:9]=1)=[O:7].O1CCCC1.[OH-].[Na+]>O.CO>[NH2:14][C:13]1[C:8]([C:6]([OH:7])=[O:5])=[N:9][CH:10]=[C:11]([NH2:15])[N:12]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 168937Lithium hydroxide, monohydrateHCID 15148126Methyl 3,5-diaminopyrazine-2-carboxylate

Product 1

HCID 21548009HCID 21548009, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Lithium hydroxide monohydrate (2.50 g, 59.5 mmol) was added to 3,5-diamino-pyrazine-2-carboxylic acid methyl ester (10.0 g, 59.5 mmol) described in Preparation Example AA-1 in a mixture solvent of tetrahydrofuran (100 mL), methanol (10 mL) and water (10 mL) at room temperature. The solution was stirred at room temperature for 17 hours, then, an aqueous solution of 5N sodium hydroxide (15 mL) was added thereto, followed by further stirring for 4.5 hours under reflux. The reaction solution was cooled to room temperature, and partitioned in 5N hydrochloric acid solution and ethyl acetate. The organic layer was separated, washed with brine, and then, dried over anhydrous magnesium sulfate. The organic layer was filtered, then, the solvent was evaporated in vacuo, and the title compound (3.34 g, 36%) was obtained as a crude product of a white solid.

Workup

  1. stirringby further stirring for 4.5 hours
  2. temperatureunder reflux
  3. temperatureThe reaction solution was cooled to room temperature
  4. custompartitioned in 5N hydrochloric acid solution
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe organic layer was filtered
  9. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-59bc8c3348da46ea884620c3a62c4058
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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