Reaction #3273

Reaction equation

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

NaH

1-Iodobutane

→

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

Yield 64.0%

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
   Washwashed with water
5. 5
   OtherThe residue was dried
6. 6
   Otherpurified by flash chromatography
7. 7
   Washeluting with a gradient of 1:1 hexane

Procedure

To a suspension of NaH (60% in mineral oil, 34 mg) in 6 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (202 mg, 0.66 mmol). The mixture was heated to 50° C., resulting in a clear solution. 1-Iodobutane (105 μL, 0.92 mmol) was added, and the solution was stirred at 50° C. for 30 minutes, then cooled to room temperature and poured onto 40 mL of ice water. The resulting precipitate was removed by filtration and washed with water. The residue was dried and purified by flash chromatography, eluting with a gradient of 1:1 hexane:ethyl acetate to all ethyl acetate to provide 152 mg (64%) of 2-amino-8-butyl-6-(2,6-dichlorophenyl)-8H-pyrido[2,3-d]pyrimidin-7-one; mp 202°-205° C.

Source