Hydrogen Bromide → HCID 5330212, compound

HRID 2300060Notes

Reaction equation

HRID 2300060 reaction equation
[CH2:1]([N:3]1[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]1=[O:22])[CH3:2].Br>C(O)(=O)CC>[CH2:1]([N:3]1[C:8]2[N:9]=[C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]1=[O:22])[CH3:2]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 5330211HCID 5330211, compound

Product 1

HCID 5330212HCID 5330212, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

A mixture of 8-ethyl-2-(4-methoxyphenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one (133 mg, 0.45 mmol) and 1 mL of 48% aqueous HBr in 10 mL of propionic acid was heated at reflux for 3 hours. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate. The aqueous layer was further extracted with ethyl acetate and the organic layers were combined and washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resultant solid was purified by dissolving in ethyl acetate and passing the solution through silica gel to provide 58 mg (46%) of 8-ethyl-2-(4 hydroxyphenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one, mp 222-224° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customthe reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate
  4. extractionThe aqueous layer was further extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resultant solid was purified
  10. dissolutionby dissolving in ethyl acetate

Sources & evidence

ORD record
ord-eeee8c9d21d34fb592aac50afa0338c1
Source dataset
uspto-grants-2002_12
Patent number
US06498163B1

Reaction notes

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