HCID 11214920, compound → HCID 11407794, compound

HRID 1243213Notes

Reaction equation

HRID 1243213 reaction equation
C([Si](C)(C)[O:6][C@H:7]1[CH2:11][CH2:10][C@H:9]([N:12]2[C:17]3=[N:18][C:19]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[N:20][CH:21]=[C:16]3[CH2:15][N:14]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[C:13]2=[O:37])[CH2:8]1)(C)(C)C>FC(F)(F)C(O)=O.ClCCl.O>[OH:6][C@H:7]1[CH2:11][CH2:10][C@H:9]([N:12]2[C:17]3=[N:18][C:19]([NH:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[N:20][CH:21]=[C:16]3[CH2:15][N:14]([C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)[C:13]2=[O:37])[CH2:8]1

Participants

5

Reactant 1

HCID 11214920HCID 11214920, compound

Product 1

HCID 11407794HCID 11407794, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

(−)-(1S,3S)-1-[3-(tert-Butyl-dimethyl-silanyloxy)-cyclopentyl]-3-(4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (445 mg, 0.82 mmol) (from Example 29g supra) was dissolved in a 25% trifluoroacetic acid in dichloromethane solution (5 mL) and water (300 μL) at 0° C. After stirring for 30 minutes the mixture was partitioned between ethyl acetate and 1 N aqueous sodium hydroxide and the pH of the aqueous layer was adjusted to 12 via the addition of solid sodium hydroxide. The organic layer was collected, dried over sodium sulfate, filtered and concentrated to a residue that was purified by chromatography with a silica gel column and a 0–100 ethyl acetate in hexanes to 0–40% tetrahydrofuran in ethyl acetate gradient to give (−)-(1S,3S)-1-(3-hydroxy-cyclopentyl)-3-(4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as a white solid. (Yield 307 mg, 86%).

Workup

  1. customwas partitioned between ethyl acetate and 1 N aqueous sodium hydroxide
  2. additionthe pH of the aqueous layer was adjusted to 12 via the addition of solid sodium hydroxide
  3. customThe organic layer was collected
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a residue that
  7. customwas purified by chromatography with a silica gel column

Sources & evidence

ORD record
ord-2722b239e9eb43368689ea20600c6eab
Source dataset
uspto-grants-2006_10
Patent number
US07115740B2

Reaction notes

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