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

HRID 3164

Reaction equation

HRID 3164 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[C:9]([OH:20])=[N:8][C:6]=2[N:7]=1.[H-].[Na+].[CH3:23]I>CN(C)C=O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[C:9](=[O:20])[N:8]([CH3:23])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178418283HCID 178418283, compound

Product 1

HCID 53278642-amino-6-(2,6-dichlorophenyl)-8-methyl-7H,8H-pyrido[2,3-d]pyrimidin-7-oneYield 49.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
65 °C

Procedure

To a mixture of 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7-ol (3.7 g) from Example 11 in dimethylformamide was added NaH (50% suspension in mineral oil, 0.64 g). The resulting slurry was heated at 65° C. for 0.5 hour until a solution formed. It was then cooled to 50° C. and a solution of methyl iodide (2.0 g) in dimethylformamide (10 mL) was added dropwise to the reaction. The reaction mixture was warmed and kept between 60° C.-80° C. for 3 hours. Upon cooling to room temperature, the reaction mixture was poured into ice water. The insoluble white product was filtered, washed with water, and recrystallized from ethanol using charcoal to give 1.9 g of 2-amino-6-(2,6-dichlorophenyl)-8-methyl-pyrido[2,3-d]pyrimidin-7(8H)-one; mp 235°-237° C.

Workup

  1. customformed
  2. temperatureIt was then cooled to 50° C.
  3. temperatureThe reaction mixture was warmed
  4. temperatureUpon cooling to room temperature
  5. filtrationThe insoluble white product was filtered
  6. washwashed with water
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6e29f6338ec248b690e8a6491c1779c2
Source dataset
uspto-grants-1998_03
Patent number
US05733914

Linked notes

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