Sodium Carbonate → 2-bromo-4-(cyclopropylmethyl)pyrido[2,3-b]pyrazin-3(4H)-one

HRID 1924464Notes

Reaction equation

HRID 1924464 reaction equation
[CH:1]1([CH2:4][N:5]2[C:10](=[O:11])[C:9](O)=[N:8][C:7]3[CH:13]=[CH:14][CH:15]=[N:16][C:6]2=3)[CH2:3][CH2:2]1.P(Br)(Br)([Br:19])=O.C(=O)([O-])[O-].[Na+].[Na+]>ClC(Cl)C>[Br:19][C:9]1[C:10](=[O:11])[N:5]([CH2:4][CH:1]2[CH2:3][CH2:2]2)[C:6]2[N:16]=[CH:15][CH:14]=[CH:13][C:7]=2[N:8]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24613Phosphorus oxybromideHCID 1785169094-(cyclopropylmethyl)-2-hydroxypyrido[2,3-b]pyrazin-3(4H)-one

Product 1

HCID 581031982-bromo-4-(cyclopropylmethyl)pyrido[2,3-b]pyrazin-3(4H)-oneYield 66.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

700 mg (3.22 mM) of 4-(cyclopropylmethyl)-2-hydroxypyrido[2,3-b]pyrazin-3(4H)-one and 972.3 mg (3.22 mM) of phosphorus oxybromide at 95% in 10 ml of dichloroethane were refluxed for 16H under stirring. The reaction mixture was then basified with an aqueous solution of sodium carbonate and the aqueous layer was extracted with dichloromethane. The organic layer was separated, 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 as eluant, to give, after evaporation, 650 mg of 2-bromo-4-(cyclopropylmethyl)pyrido[2,3-b]pyrazin-3(4H)-one as a white solid. Yield: 66.5%.

Workup

  1. extractionthe aqueous layer was extracted with dichloromethane
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried on anhydrous sodium sulfate
  5. customthe solvent was removed under vacuum
  6. customThe compound was further purified by silica gel column chromatography
  7. customto give
  8. customafter evaporation, 650 mg of 2-bromo-4-(cyclopropylmethyl)pyrido[2,3-b]pyrazin-3(4H)-one as a white solid

Sources & evidence

ORD record
ord-13a5bb30147e42ff82c60a77c49588ce
Source dataset
uspto-grants-2012_05
Patent number
US08178556B2

Reaction notes

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