Water → HCID 5330215, compound

HRID 2300061Notes

Reaction equation

HRID 2300061 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]([OH:20])=[CH:16][CH:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]1=[O:21])[CH3:2].[CH3:22][O:23][CH2:24][CH2:25]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[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][CH2:25][CH2:24][O:23][CH3:22])=[CH:16][CH:15]=3)[N:11]=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]1=[O:21])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 5330212HCID 5330212, compound

Product 1

HCID 5330215HCID 5330215, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-ethyl-2-(4-hydroxyphenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one (92 mg, 0.33 mmol), 2-methoxyethyl bromide (55 mg, 0.40 mmol) and potassium carbonate (360 mg, 2.61 mmol) in 5 mL of dimethylformamide was heated at reflux for 5 minutes. After cooling to room temperature, water was added, and the resultant solid collected by filtration. The solid was dissolved in ethyl acetate and the solution dried over magnesium sulfate, filtered, concentrated, and purified by flash chromatography eluting with ethyl acetate to provide 92 mg (56%) of 8-ethyl-2-[4-(2-methoxyethoxy)phenylamino]-8H-pyrido[2,3-d]pyrimidin-7-one, mp 169-171° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 minutes
  3. filtrationthe resultant solid collected by filtration
  4. dissolutionThe solid was dissolved in ethyl acetate
  5. dry with materialthe solution dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash chromatography
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-868eeaa6d69f424c8b9e1dc272cad064
Source dataset
uspto-grants-2002_12
Patent number
US06498163B1

Reaction notes

Loading…