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Ammonium formate → 1-Propyl-8-[6-(3-trifluoromethyl-benzylamino)-pyridin-3-yl]-1,7-dihydro-purin-6-one

HRID 536013
Notes
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Reaction equation

HRID 536013 reaction equation
Cl[C:2]1[N:3]([CH2:30][CH2:31][CH3:32])[C:4](=[O:29])[C:5]2[NH:6][C:7]([C:11]3[CH:12]=[N:13][C:14]([NH:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=4)=[CH:15][CH:16]=3)=[N:8][C:9]=2[N:10]=1.C([O-])=O.[NH4+]>[Pd].CN(C=O)C>[CH2:30]([N:3]1[C:4](=[O:29])[C:5]2[NH:6][C:7]([C:11]3[CH:12]=[N:13][C:14]([NH:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=4)=[CH:15][CH:16]=3)=[N:8][C:9]=2[N:10]=[CH:2]1)[CH2:31][CH3:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 674981072-Chloro-1-propyl-8-[6-(3-trifluoromethyl-benzylamino)-pyridin-3-yl]-1,7-dihydro-purin-6-one

Product 1

HCID 671349991-Propyl-8-[6-(3-trifluoromethyl-benzylamino)-pyridin-3-yl]-1,7-dihydro-purin-6-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-Chloro-1-propyl-8-[6-(3-trifluoromethyl-benzylamino)-pyridin-3-yl]-1,7-dihydro-purin-6-one (0.094 g, 0.2 mmol), Ammonium formate (0.256 g, 0.4 mmol), Pd/C (0.094 g) and DMF (4 ml) were stirred for 30 minutes at 60° C. The reaction mixture was cooled to room temperature and filtered through celite bed. The organic volatiles were evaporated and the residue was acidified with citric acid. The solid precipitated out was filtered to get pure 1-Propyl-8-[6-(3-trifluoromethyl-benzylamino)-pyridin-3-yl]-1,7-dihydro-purin-6-one as off white solid (16 mg, 40%). 1HNMR (400 MHz, DMSO d6): δ 0.84-0.90 (m, 3H); 1.66-1.73 (m, 2H); 3.94-3.99 (m, 2H); 4.65 (d, J=5.6 Hz, 2H); 6.66 (d, J=9.2 Hz, 1H); 7.55-7.79 (m, 4H); 8.13 (dd, J=8.8 Hz, 2.4 Hz, 1H); 8.30 (s, 1H); 8.78 (d, J=2.4 Hz, 1H); 13.56 (s, 1H)

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through celite bed
  3. customThe organic volatiles were evaporated
  4. customThe solid precipitated out
  5. filtrationwas filtered

Sources & evidence

ORD record
ord-f7c46d96efeb430ebe7740707811b04a
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08859566B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes