Ammonium formate → 8-ethoxy-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione

HRID 2200592Notes

Reaction equation

HRID 2200592 reaction equation
C([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][OH:21])[C:13](=[O:22])[N:12]([CH2:23][CH3:24])[C:11]=2[N:10]=[C:9]1[O:25][CH2:26][CH3:27])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH2:26]([O:25][C:9]1[NH:8][C:16]2[C:15](=[O:17])[N:14]([CH2:18][CH2:19][CH2:20][OH:21])[C:13](=[O:22])[N:12]([CH2:23][CH3:24])[C:11]=2[N:10]=1)[CH3:27]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 904023587-benzyl-8-ethoxy-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 904023668-ethoxy-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dioneYield 77.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

7-benzyl-8-ethoxy-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione (0.12 g, 0.323 mmol) was dissolved in ethanol (20 mL) and degassed and refilled with nitrogen three times. Ammonium formate (0.5 g, 7.94 mmol) and 10% Pd/C (30 mg) were added and the mixture was again degassed and refilled with nitrogen three times. The reaction was stirred at 80° C. overnight. Then the mixture was cooled, filtered and the filter cake was washed with methanol. The filtrate was concentrated to give 8-ethoxy-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione (70 mg, 77.1% yield) as white solid. LCMS retention time 0.413 min; LCMS MH+ 283.

Workup

  1. customdegassed
  2. additionrefilled with nitrogen three times
  3. customthe mixture was again degassed
  4. additionrefilled with nitrogen three times
  5. temperatureThen the mixture was cooled
  6. filtrationfiltered
  7. washthe filter cake was washed with methanol
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-bcbf64cc3c114bf9977d6ac59b3a5747
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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