Sodium Hydroxide → 8-{4-[1-(4-Fluorophenyl)-5-oxo-pyrrolidin-3-ylmethoxy]phenyl}-1,3-dipropyl-3,7-dihydropurine-2,6-dione

HRID 889041Notes

Reaction equation

HRID 889041 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6](=[O:11])[N:5]([CH2:12][CH2:13][CH3:14])[C:4](=[O:15])[C:3]=1[NH:16][C:17](=O)[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]2[CH2:30][C:29](=[O:31])[N:28]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[CH2:27]2)=[CH:20][CH:19]=1.[OH-].[Na+]>CO>[F:38][C:35]1[CH:36]=[CH:37][C:32]([N:28]2[C:29](=[O:31])[CH2:30][CH:26]([CH2:25][O:24][C:21]3[CH:22]=[CH:23][C:18]([C:17]4[NH:16][C:3]5[C:4](=[O:15])[N:5]([CH2:12][CH2:13][CH3:14])[C:6](=[O:11])[N:7]([CH2:8][CH2:9][CH3:10])[C:2]=5[N:1]=4)=[CH:19][CH:20]=3)[CH2:27]2)=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57988770N-(6-Amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-4-[1-(4-fluoro-phenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzamide

Product 1

HCID 579887768-{4-[1-(4-Fluorophenyl)-5-oxo-pyrrolidin-3-ylmethoxy]phenyl}-1,3-dipropyl-3,7-dihydropurine-2,6-dioneYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(6-Amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-4-[1-(4-fluoro-phenyl)-5-oxo-pyrrolidin-3-ylmethoxy]-benzamide obtained in step 3 (0.90 g, 0.167 mmol) was dissolved in MeOH (4 mL) and 10% NaOH (0.020 g, 0.502 mmol) and stirred at 80° C. for 7 h. MeOH was distilled off and the residue was taken up in H2O (2 mL), acidified with 2NHC1 to pH 4-5. The precipitate was filtered, washed with water and methanol to provide the title compound as white solid (0.072 g, 83%).

Workup

  1. distillationMeOH was distilled off
  2. filtrationThe precipitate was filtered
  3. washwashed with water and methanol

Sources & evidence

ORD record
ord-20f75d7557dd461e91daae7b5cf65cf7
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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