Ammonium formate → 9-Deazaguanine

HRID 1516836Notes

Reaction equation

HRID 1516836 reaction equation
[NH2:1][C:2]1[N:3](CC2C=CC=CC=2)[C:4](=[O:11])[C:5]2[NH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:1][C:2]1[NH:3][C:4](=[O:11])[C:5]2[NH:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 153761052-Amino-3-benzyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one

Product 1

HCID 1354610039-DeazaguanineYield 103.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 2-amino-3-benzyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (10 g, 0.04 mol) in MeOH (334 mL) was added 10% Pd/C (2 g), ammonium formate (13.2 g, 0.21 mmol) and heated at 75° C. for 4 h. After completion of the reaction, the reaction mixture was cooled and filtered through a pad of Celite with hot 1:1 DMF/MeOH. The filtrate was concentrated in vacuo to provide the product as an off-white solid (6.2 g, 99%).

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction mixture was cooled
  3. filtrationfiltered through a pad of Celite with hot 1:1 DMF/MeOH
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b074921f184243c5ac90f1fb9f1a6aec
Source dataset
uspto-grants-2012_07
Patent number
US08227601B2

Reaction notes

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