Water → 3-(4-methoxy-phenyl)-7-phenylamino-1-piperidin-4-yl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 1243162Notes

Reaction equation

HRID 1243162 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([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])[CH2:10][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:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[C:15]2=[O:39])=[CH:36][CH:35]=1

Participants

5

Reactant 2

HCID 962WaterHCID 11237883HCID 11237883, compound

Product 1

HCID 111663063-(4-methoxy-phenyl)-7-phenylamino-1-piperidin-4-yl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4-[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 mmol) (from Example 2a supra) was dissolved at 0° C. in a 50% solution of trifluoroacetic acid in dichloromethane (6 mL) that contained 100 μL of water. After stirring for 1.5 hours the mixture was partitioned between ethyl acetate and 1 N aqueous sodium hydroxide and the pH of the aqueous layer was adjusted to 12 by the addition of solid sodium hydroxide. The organic layer was then washed with water, dried over sodium sulfate, filtered and concentrated. The crude material was purified by precipitation out of tetrahydrofuran with excess of pentane to give 3-(4-methoxy-phenyl)-7-phenylamino-1-piperidin-4-yl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as an off white solid. (Yield 42 mg, 75%).

Workup

  1. customwas partitioned between ethyl acetate and 1 N aqueous sodium hydroxide
  2. additionthe pH of the aqueous layer was adjusted to 12 by the addition of solid sodium hydroxide
  3. washThe organic layer was then washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by precipitation out of tetrahydrofuran with excess of pentane

Sources & evidence

ORD record
ord-01867d03774c421c910eaa954abb650e
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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