Methanol → 4-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid methyl ester

HRID 480108Notes

Reaction equation

HRID 480108 reaction equation
[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[N:8]=[C:7]([C:14]34[CH2:21][CH2:20][C:17]([C:22]([OH:24])=[O:23])([CH2:18][CH2:19]3)[CH2:16][CH2:15]4)[NH:6][C:5]=2[C:4](=[O:25])[N:3]1[CH2:26][CH2:27][CH3:28].CO.[C:31]([O-])(O)=O.[Na+]>OS(O)(=O)=O.CCOC(C)=O>[CH3:31][O:23][C:22]([C:17]12[CH2:20][CH2:21][C:14]([C:7]3[NH:6][C:5]4[C:4](=[O:25])[N:3]([CH2:26][CH2:27][CH3:28])[C:2](=[O:1])[N:10]([CH2:11][CH2:12][CH3:13])[C:9]=4[N:8]=3)([CH2:19][CH2:18]1)[CH2:15][CH2:16]2)=[O:24]

Participants

6

Reactant 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 98865894-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid

Product 1

HCID 98440604-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid methyl esterYield 97%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]octane-1-carboxylic acid (Example 13) (1.50 g, 3.86 mmol) was combined with 60 ml of MeOH, and 10 drops of conc'd H2SO4. The reaction solution was brought to reflux until consumption of starting material ceased. Sat'd NaHCO3 was then added until neutral pH and the reaction mixture was conc'd in vacuo. The residue was taken up in EtOAc and washed with sat'd NaHCO3, brine, and dried over Na2SO4. The EtOAc solution was conc'd in vacuo to give 1.51 g (97% yield) of a white solid. (MH+=403.13)

Workup

  1. temperatureto reflux until consumption of starting material
  2. washwashed with sat'd NaHCO3, brine
  3. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-86dbde1489974cb09f8bfc93938ff989
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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