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

HRID 1586415Notes

Reaction equation

HRID 1586415 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]([OH:22])=[N:10][C:8]=2[N:9]=1.I[CH2:24][CH2:25][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:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[C:11](=[O:22])[N:10]([CH2:24][CH2:25][CH3:26])[C:8]=2[N:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 178418283HCID 178418283, compound

Product 1

HCID 53286262-amino-6-(2,6-dichlorophenyl)-8-propyl-7H,8H-pyrido[2,3-d]pyrimidin-7-oneYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of NaH (60% in mineral oil, 31 mg) in 6 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one from Example 11 (205 mg, 0.67 mmol). The mixture was heated at 50° C. for 1 hour resulting in a clear solution. 1-Iodopropane (100 μL, 1.03 mmol) was added, and the solution was stirred at 50° C. for 10 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 1:1 hexane:ethyl acetate to provide 159 mg (68%) of 2-amino-6-(2,6-dichlorophenyl)-8-propyl-8H-pyrido[2,3-d]pyrimidin-7-one; mp 196-197° C.

Workup

  1. customresulting in a clear solution
  2. temperaturecooled to room temperature
  3. customThe resulting precipitate was removed by filtration
  4. washwashed with water
  5. customThe residue was dried
  6. custompurified by flash chromatography
  7. washeluting with 1:1 hexane

Sources & evidence

ORD record
ord-059ee542492d47159aa76af37d03abb3
Source dataset
uspto-grants-1999_08
Patent number
US05945422

Reaction notes

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