Sodium Hydroxide → HCID 10436326, compound

HRID 459968Notes

Reaction equation

HRID 459968 reaction equation
[CH:1]1([N:6]2[C:11]3=[N:12][C:13]([NH:16][CH2:17][C@H:18]4[CH:22]([CH2:23][OH:24])[O:21][C@@H](C5C=CC=CC=5)[O:19]4)=[N:14][CH:15]=[C:10]3[CH2:9][N:8]([C:31]3[C:36]([F:37])=[C:35]([O:38][CH3:39])[CH:34]=[C:33]([O:40][CH3:41])[C:32]=3[F:42])[C:7]2=[O:43])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([N:6]2[C:11]3=[N:12][C:13]([NH:16][CH2:17][C@H:18]([OH:19])[C@@H:22]([OH:21])[CH2:23][OH:24])=[N:14][CH:15]=[C:10]3[CH2:9][N:8]([C:31]3[C:36]([F:37])=[C:35]([O:38][CH3:39])[CH:34]=[C:33]([O:40][CH3:41])[C:32]=3[F:42])[C:7]2=[O:43])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86590946HCID 86590946, compound

Product 1

HCID 10436326HCID 10436326, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(S,S)-1-Cyclopentyl-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-7-[(5-hydroxymethyl-2-phenyl-[1,3]dioxolan-4-ylmethyl)-amino]-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one (0.57 g, 0.95 mmol) was dissolved in 90 mL methanol containing 12 mL 10% HCl acid. The mixture was stirred at room temperature for 9 hours. Adjusted pH=12 by adding 1 M NaOH. Stripped the solvent. The residue was dissolved in methanol. Insoluble NaCl was removed by filtration. The filtrate was evaporated to dryness and the residue was purified by column chromatography (5:1 dichloromethane/methanol) to give 0.275 g (57%) (S,S)-1-cyclopentyl-3-(2,6-difluoro-3,5-dimethoxy-phenyl)-7-(2,3,4-trihydroxy-butylamino)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one as white solid: mp=160° C (dec.); MS (APCI) m/z 510.1, 511.1.

Workup

  1. customInsoluble NaCl was removed by filtration
  2. customThe filtrate was evaporated to dryness
  3. customthe residue was purified by column chromatography (5:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-30649a54e4da47a189853c970864f6c0
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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