Water → HCID 11235766, compound

HRID 1243165Notes

Reaction equation

HRID 1243165 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([N:14]2[C:19]3=[N:20][C:21]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:22][CH:23]=[C:18]3[CH2:17][N:16]([C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)[C:15]2=[O:39])[CH2:9]1)=O)(C)(C)C.O>FC(F)(F)C(O)=O.ClCCl>[CH3:38][O:37][C:34]1[CH:33]=[CH:32][C:31]([N:16]2[CH2:17][C:18]3[C:19](=[N:20][C:21]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:22][CH:23]=3)[N:14]([CH:10]3[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]3)[C:15]2=[O:39])=[CH:36][CH:35]=1

Participants

5

Reactant 2

HCID 962WaterHCID 11295502HCID 11295502, compound

Product 1

HCID 11235766HCID 11235766, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

3-[3-(4-Methoxy-phenyl)-2-oxo-7-phenylamino-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (70 mg, 0.13 mmols) (from Example 4a supra) was dissolved at 0° C. in a 50% trifluoroacetic acid in dichloromethane solution (5 mL) that contained water (300 μL). After stirring for 1.5 hours the reaction mixture was partitioned between ethyl acetate and 1 N aqueous sodium hydroxide and the pH of the aqueous layer was adjusted to 12 by adding solid sodium hydroxide. The organic layer was then washed with water, dried over sodium sulfate, filtered and concentrated to the crude product. This material was dissolved in tetrahydrofuran and precipitated with an excess of pentane to give 3-(4-methoxy-phenyl)-7-phenylamino-1-piperidin-3-yl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as an off-white solid. (Yield 47 mg, 84%).

Workup

  1. customwas partitioned between ethyl acetate and 1 N aqueous sodium hydroxide
  2. additionby adding solid sodium hydroxide
  3. washThe organic layer was then washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to the crude product
  7. dissolutionThis material was dissolved in tetrahydrofuran
  8. customprecipitated with an excess of pentane

Sources & evidence

ORD record
ord-05bc62d564b742e9b469f59aac6245ab
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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