Methyl iodide → 3-(4-methoxy-phenyl)-1-methyl-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidine-2-one

HRID 1243196Notes

Reaction equation

HRID 1243196 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:18][C:17]3[C:12](=[N:13][C:14]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[N:15][CH:16]=3)[NH:11][C:10]2=[O:26])=[CH:5][CH:4]=1.[H-].[Na+].[CH3:29]I>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:18][C:17]3[C:12](=[N:13][C:14]([NH:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[N:15][CH:16]=3)[N:11]([CH3:29])[C:10]2=[O:26])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9863083HCID 9863083, compound

Product 1

HCID 112798993-(4-methoxy-phenyl)-1-methyl-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidine-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the suspension of 3-(4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (34.7 mg, 0.1 mmol) (from Example 24a supra) in tetrahydrofuran (5 mL) was added sodium hydride (60%, 10 mg, 0.25 mmol) (Aldrich) followed by methyl iodide (0.032 mL, 0.5 mmol) (Aldrich) in one portion. The reaction mixture was stirred at room temperature overnight and then heated under reflux for 5 hours. The reaction was then quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate (3×50 mL). The combined organic extracts were filtered to give 3-(4-methoxy-phenyl)-1-methyl-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidine-2-one as a white solid. (Yield 20.9 mg, 57.9%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. customThe reaction was then quenched with saturated aqueous ammonium chloride solution
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. filtrationThe combined organic extracts were filtered

Sources & evidence

ORD record
ord-e4e07a478fca48958b0a05101ab8203f
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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