Ammonium formate → 9-Deazaguanine
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]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- customAfter completion of the reaction
- temperaturethe reaction mixture was cooled
- filtrationfiltered through a pad of Celite with hot 1:1 DMF/MeOH
- concentrationThe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-b35458de54f34030b1164974712f393d
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354532B2
Reaction notes
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