Water → 4-(cyclopropylmethyl)-2-hydroxypyrido[2,3-b]pyrazin-3(4H)-one

HRID 1924463Notes

Reaction equation

HRID 1924463 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]2[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][N:7]=2)[CH2:3][CH2:2]1.C(NC(C)C)(C)C.Cl[C:21](=[O:27])[C:22](OCC)=[O:23].O>ClCCl>[CH:1]1([CH2:4][N:5]2[C:22](=[O:23])[C:21]([OH:27])=[N:12][C:11]3[CH:10]=[CH:9][CH:8]=[N:7][C:6]2=3)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 7912DiisopropylamineHCID 20884Ethoxalyl chlorideHCID 28902457N2-(cyclopropylmethyl)pyridine-2,3-diamine

Product 1

HCID 1785169094-(cyclopropylmethyl)-2-hydroxypyrido[2,3-b]pyrazin-3(4H)-oneYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1.6 g (9.8 mM) of N2-(cyclopropylmethyl)pyridine-2,3-diamine and 1.7 ml (9.8 mM) of diisopropylamine in 20 ml of dichloromethane were added, drop by drop, under stirring; at room temperature, 1.1 ml (9.8 mM) of ethyl chloro(oxo)acetate. The reaction mixture was stirred at room temperature for 16 h and water was added. The organic layer was separated and the aqueous layer was extracted twice with dichloromethane. The combined organic layer was washed with water, dried on anhydrous sodium sulfate and the solvent was removed under vacuum. The compound was further purified by silica gel column chromatography using dichloromethane/methanol (95/5) as eluant, which afforded after evaporation 700 mg of 4-(cyclopropylmethyl)-2-hydroxypyrido[2,3-b]pyrazin-3(4H)-one as a solid. Yield: 33%.

Workup

  1. customat room temperature
  2. stirringThe reaction mixture was stirred at room temperature for 16 h
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted twice with dichloromethane
  5. washThe combined organic layer was washed with water
  6. dry with materialdried on anhydrous sodium sulfate
  7. customthe solvent was removed under vacuum
  8. customThe compound was further purified by silica gel column chromatography
  9. customwhich afforded
  10. customafter evaporation 700 mg of 4-(cyclopropylmethyl)-2-hydroxypyrido[2,3-b]pyrazin-3(4H)-one as a solid

Sources & evidence

ORD record
ord-318747180d0b4508983ace56185214f4
Source dataset
uspto-grants-2012_05
Patent number
US08178556B2

Reaction notes

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