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

HRID 3178

Reaction equation

HRID 3178 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:5]=[CH:6][C:7]2[CH:13]=[C:12]([C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[C:11](=[O:22])[NH:10][C:8]=2[N:9]=1.I[CH2:24][CH:25]([CH3:27])[CH3:26]>CN(C)C=O>[NH2:3][C:4]1[N:5]=[CH:6][C:7]2[CH:13]=[C:12]([C:14]3[C:15]([Cl:21])=[CH:16][CH:17]=[CH:18][C:19]=3[Cl:20])[C:11](=[O:22])[N:10]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:8]=2[N:9]=1

Participants

5

Reactant 3

HCID 10556Isobutyl iodide2×HCID 24758Sodium hydrideHCID 104949152-Amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7-ol

Product 1

HCID 53286282-amino-6-(2,6-dichlorophenyl)-8-isobutyl-8H-pyrido[2,3-d]pyrimidin-7-oneYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of NaH (60% in mineral oil, 36 mg) in 8 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (205 mg, 0.67 mmol). The mixture was heated at 60° C. for 20 minutes resulting in a clear solution. 1-Iodo-2-methylpropane (110 μL, 0.94 mmol) was added, and the solution was stirred at 50° C. for 30 minutes. An additional amount of 1-iodo-2-methylpropane (40 μL, 0.34 mmol) was added, and the solution was stirred at 50° C. for 40 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 gummy residue was dissolved in ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting solid was purified by flash chromatography, eluting with 1:1 hexane:ethyl acetate to provide 123 mg (51%) of 2-amino-6-(2,6-dichlorophenyl)-8-isobutyl-8H-pyrido[2,3-d]pyrimidin-7-one; mp 193°-195° C.

Workup

  1. customresulting in a clear solution
  2. stirringthe solution was stirred at 50° C. for 40 minutes
  3. temperaturecooled to room temperature
  4. customThe resulting precipitate was removed by filtration
  5. washwashed with water
  6. dissolutionThe gummy residue was dissolved in ethyl acetate
  7. washwashed with water
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe resulting solid was purified by flash chromatography
  12. washeluting with 1:1 hexane

Sources & evidence

ORD record
ord-398313438a35477a99dae3e5237c331e
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Linked notes

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