1,1'-Carbonyldiimidazole → Ethyl 2-(6-bromo-2-oxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)acetate

HRID 83016Notes

Reaction equation

HRID 83016 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[NH2:13][C:14]1[C:19]([CH2:20][NH:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:18][C:17]([Br:28])=[CH:16][N:15]=1>O1CCOCC1>[Br:28][C:17]1[CH:16]=[N:15][C:14]2[NH:13][C:6](=[O:7])[N:21]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:20][C:19]=2[CH:18]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59456921Ethyl 2-((2-amino-5-bromopyridin-3-yl)methylamino)acetate

Product 1

HCID 66966289Ethyl 2-(6-bromo-2-oxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)acetateYield 56%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

CDI (1.8 g, 114 mmol) was added to a solution of ethyl 2-((2-amino-5-bromopyridin-3-yl)methylamino)acetate (1.1 g, 38.17 mmol) in dioxane (36 mL). The reaction mixture was stirred at reflux for 5 hours and then concentrated to dryness. The residue was partitioned between dichloromethane (40 mL) and water (30 mL). The aqueous phase was separated and extracted with dichloromethane (2×30 mL). The combined organic phases were washed with brine (50 mL), dried over sodium sulfate, filtered and concentrated to dryness. The isolated compound was finally precipitated from a mixture dichloromethane/pentane to give the title product as a yellow solid (670 mg, 56%).

Workup

  1. temperatureat reflux for 5 hours
  2. concentrationconcentrated to dryness
  3. customThe residue was partitioned between dichloromethane (40 mL) and water (30 mL)
  4. customThe aqueous phase was separated
  5. extractionextracted with dichloromethane (2×30 mL)
  6. washThe combined organic phases were washed with brine (50 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customThe isolated compound was finally precipitated from a mixture dichloromethane/pentane

Sources & evidence

ORD record
ord-885237438e8442da920aad2e60ce7c4d
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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