Sodium hydride → 8-(3-Phenoxypropyl)-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 2300076Notes

Reaction equation

HRID 2300076 reaction equation
[H-].[Na+].[C:3]1([NH:9][C:10]2[N:11]=[CH:12][C:13]3[CH:19]=[CH:18][C:17](=[O:20])[NH:16][C:14]=3[N:15]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:21]([CH2:28][CH2:29][CH2:30]Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[O:21]([CH2:28][CH2:29][CH2:30][N:16]1[C:14]2[N:15]=[C:10]([NH:9][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:11]=[CH:12][C:13]=2[CH:19]=[CH:18][C:17]1=[O:20])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 68522Benzene, (3-bromopropoxy)-HCID 105140732-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 183747698-(3-Phenoxypropyl)-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of NaH (51 mg of a 60% suspension of NaH in mineral oil) in 6 mL of dimethylformamide was added 2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one (200 mg, 0.84 mmol). The reaction mixture was heated to 50° C. resulting in a yellow solution. The solution was cooled slightly, and 3-phenoxypropyl bromide (230 μL, 1.47 mmol) was added. The reaction mixture was heated at 50° C. for 10 minutes, then cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Methanol and ethyl acetate were added to the residue, and 60 mg (19%) of 8-(3-phenoxypropyl)-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one was collected by filtration, mp 175-176° C.

Workup

  1. customresulting in a yellow solution
  2. temperatureThe solution was cooled slightly
  3. temperatureThe reaction mixture was heated at 50° C. for 10 minutes
  4. temperaturecooled to room temperature
  5. custompartitioned between water and ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. additionMethanol and ethyl acetate were added to the residue, and 60 mg (19%) of 8-(3-phenoxypropyl)-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one
  10. filtrationwas collected by filtration, mp 175-176° C.

Sources & evidence

ORD record
ord-8be5717a1dc0407381958bb89376b357
Source dataset
uspto-grants-2002_12
Patent number
US06498163B1

Reaction notes

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