Phosphorus oxybromide → 2,6-Dibromopyrido[3,2-d]pyrimidine

HRID 1799579Notes

Reaction equation

HRID 1799579 reaction equation
P(Br)(Br)([Br:3])=O.[Br:6][C:7]1[N:8]=[CH:9][C:10]2[N:16]=[C:15](O)[CH:14]=[CH:13][C:11]=2[N:12]=1>CN(C)C=O>[Br:6][C:7]1[N:8]=[CH:9][C:10]2[N:16]=[C:15]([Br:3])[CH:14]=[CH:13][C:11]=2[N:12]=1

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178515741HCID 178515741, compound

Product 1

HCID 582166532,6-Dibromopyrido[3,2-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A roundbottom flask was charged with N,N-dimethylformamide (4.2 L). Phosphorus oxybromide (646.9 g, 2.26 mol, 2.30 equiv) was added followed by dropwise addition of 2-bromopyrido-[3,2-d]-pyrimidin-6-ol (170 g, 752.1 mmol). The resulting solution was allowed to react, with stirring, for 1 minute while the temperature was maintained at 90° C. The reaction mixture was then quenched by the addition of 10 L of water/ice. The resulting solution was extracted once with ethyl acetate. The organic layer was washed with aqueous NaHSO4 and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified via silica gel chromatography eluting with dichloromethane to afford the title compound.

Workup

  1. customto react
  2. customThe reaction mixture was then quenched by the addition of 10 L of water/ice
  3. extractionThe resulting solution was extracted once with ethyl acetate
  4. washThe organic layer was washed with aqueous NaHSO4 and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified via silica gel chromatography
  9. washeluting with dichloromethane

Sources & evidence

ORD record
ord-579b20a13c7043d8a2376b614c34b18b
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

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