5-(6-Amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester → 5-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[3.2.1]octane-1-carboxylic acid

HRID 2105635Notes

Reaction equation

HRID 2105635 reaction equation
C([O:3][C:4]([C:6]12[CH2:13][C:10]([C:14](=O)[NH:15][C:16]3[C:17](=[O:30])[N:18]([CH2:27][CH2:28][CH3:29])[C:19](=[O:26])[N:20]([CH2:23][CH2:24][CH3:25])[C:21]=3[NH2:22])([CH2:11][CH2:12]1)[CH2:9][CH2:8][CH2:7]2)=[O:5])C>[OH-].[Na+].CO>[O:26]=[C:19]1[N:20]([CH2:23][CH2:24][CH3:25])[C:21]2[N:22]=[C:14]([C:10]34[CH2:13][C:6]([C:4]([OH:3])=[O:5])([CH2:12][CH2:11]3)[CH2:7][CH2:8][CH2:9]4)[NH:15][C:16]=2[C:17](=[O:30])[N:18]1[CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 1

HCID 670783425-(6-Amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester

Product 1

HCID 98432695-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[3.2.1]octane-1-carboxylic acidYield 42.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 5-(6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester (0.238 mmol, 0.10 g) in 20% NaOH (2.0 ml) and MeOH (10.0 ml) was stirred and refluxed 5 h. The reaction was cooled to room temperature and then concentrated to remove MeOH. The aqueous was acidified (pH 2-3) with conc. HCl and then extracted with EtOAc. The combined EtOAc extracts were washed with H2O and brine, and dried (MgSO4). Filtration and evaporation followed by reverse phase HPLC provided product (0.039 g, 42%) as a solid.

Workup

  1. temperaturerefluxed 5 h
  2. concentrationconcentrated
  3. customto remove MeOH
  4. extractionextracted with EtOAc
  5. washThe combined EtOAc extracts were washed with H2O and brine
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-4b9fc821cad549c4b9338fd4a4d8d7fb
Source dataset
uspto-grants-2009_08
Patent number
US07579354B2

Reaction notes

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