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

HRID 925560
Notes
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Reaction equation

HRID 925560 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-9ef37503bac148dea452a2de68aecb0a
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09284316B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes