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Water → (+)-(1R,3R)-1-(3-hydroxy-cyclopentyl)-3-(4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 1243204
Notes
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Reaction equation

HRID 1243204 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.O>FC(F)(F)C(O)=O.ClCCl>[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 962WaterHCID 11238111(-)-(1R,3R)-1-[3-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-3-(4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

Product 1

HCID 9910609(+)-(1R,3R)-1-(3-hydroxy-cyclopentyl)-3-(4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent
HCID 6422
Trifluoroacetic acid
Solvent

Procedure

(−)-(1R,3R)-1-[3-(tert-Butyl-dimethyl-silanyloxy)-cyclopentyl]-3-(4-methoxy-phenyl)-7-phenylamino-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (148 mg, 0.27 mmol) (from Example 27e supra) was dissolved at 0° C. in a 25% trifluoroacetic acid in dichloromethane solution (5 mL) that contained water (300 μL). After stirring for 30 minutes the reaction mixture was partitioned between ethyl acetate and 0.5 N aqueous sodium hydroxide. The pH of the aqueous layer was adjusted to 12 via the addition of solid sodium hydroxide. The organic layer was then collected, dried over sodium sulfate, filtered and concentrated to give the crude product. Purification by silica gel column chromatography using a 0–100% ethyl acetate in hexanes to 0–40% tetrahydrofuran in ethyl acetate gradient followed by a precipitation out of dichloromethane with excess pentane afforded (+)-(1R,3R)-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 92 mg, 86%).

Workup

  1. customwas partitioned between ethyl acetate and 0.5 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 then collected
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product
  8. customPurification by silica gel column chromatography
  9. customfollowed by a precipitation out of dichloromethane with excess pentane

Sources & evidence

ORD record
ord-934846f3585240d4ab68dfddd9553546
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07115740B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes