Reaction #3271

Reaction equation

2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one

2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7-ol

NaH

Ethyl iodide

→

2-amino-6-(2,6-dichlorophenyl)-8-ethyl-pyrido[2,3-d]pyrimidin-7(8H)-one

Yield 55.4%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   Otherresulting in a clear solution
2. 2
   Temperaturecooled to room temperature
3. 3
   OtherThe resulting precipitate was removed by filtration
4. 4
   Otherpartitioned between ethyl acetate and water
5. 5
   OtherThe organic layer was separated
6. 6
   Dryingdried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated in vacuo
9. 9
   WashFlash chromatography, eluting with ethyl acetate

Procedure

To a suspension of NaH (60% in mineral oil, 27 mg) in 5 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (172 mg, 0.56 mmol) from Example 11. The mixture was heated at 50° C. for 1 hour resulting in a clear solution. Ethyl iodide (60 μL, 0.75 mmol) was added, and the solution was stirred at 50° C. for 3.5 hours, cooled to room temperature, and poured into 30 mL of ice water. The resulting precipitate was removed by filtration and partitioned between ethyl acetate and water. The organic layer was separated and dried over MgSO4, filtered, and concentrated in vacuo. Flash chromatography, eluting with ethyl acetate, provided 104 mg (55%) of 2-amino-6-(2,6-dichlorophenyl)-8-ethyl-pyrido[2,3-d]pyrimidin-7(8H)-one; mp 207°-209° C.

Source