Acetic Anhydride → HCID 9982567, compound

HRID 2216996Notes

Reaction equation

HRID 2216996 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:18]([CH3:19])[C:17]3[C:12](=[N:13][C:14]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:15][CH:16]=3)[N:11]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:10]2=[O:33])=[CH:5][CH:4]=1.[C:34](OC(=O)C)(=[O:36])[CH3:35]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:18]([CH3:19])[C:17]3[CH:16]=[N:15][C:14]([N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:34](=[O:36])[CH3:35])=[N:13][C:12]=3[N:11]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:10]2=[O:33])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 9867727HCID 9867727, compound

Product 1

HCID 9982567HCID 9982567, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of (±)-3-(4-methoxy-phenyl)-4-methyl-1-phenyl-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (500 mg, 1.14 mmol) (from Example 1g supra) in pyridine (1 mL) (Fisher) was added acetic anhydride (1.0 mL) followed by addition of 4-(dimethylamino)pyridine (25 mg) (Aldrich) in one portion. The reaction mixture was heated to 90° C. for 5 hours until no starting material was detectable by TLC analysis. The reaction mixture was quenched with water and extracted with ethyl acetate (3×50 mL). The combined organic extracts were successively washed with water (10 mL) and brine (10 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give the crude product which was purified by flash chromatography to give (±)-N-[6-(4-methoxy-phenyl)-5-methyl-7-oxo-8-phenyl-5,6,7,8-tetrahydro-pyrimido[4,5-d]pyrimidin-2-yl]-N-phenyl-acetamide. (Yield 373 mg, 68.0%).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organic extracts were successively washed with water (10 mL) and brine (10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product which
  8. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-6c01c6e90e10450ab203db0a09d5251e
Source dataset
uspto-grants-2006_09
Patent number
US07112676B2

Reaction notes

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