Sodium Iodide → 6-Oxo-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-6,7-dihydro-1H-purine-2-carbonitrile

HRID 536028Notes

Reaction equation

HRID 536028 reaction equation
Cl[C:2]1[N:3]([CH2:28][CH2:29][CH3:30])[C:4](=[O:27])[C:5]2[NH:6][C:7]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=4)[CH:15]=3)=[N:8][C:9]=2[N:10]=1.[C-]#N.[Na+].[Na+].[I-].[CH3:36][N:37](C=O)C>O>[O:27]=[C:4]1[N:3]([CH2:28][CH2:29][CH3:30])[C:2]([C:36]#[N:37])=[N:10][C:9]2[N:8]=[C:7]([C:11]3[CH:12]=[N:13][N:14]([CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=4)[CH:15]=3)[NH:6][C:5]1=2

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 668032942-Chloro-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-1,7-dihydro-purin-6-one

Product 1

HCID 668035696-Oxo-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-6,7-dihydro-1H-purine-2-carbonitrileYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-Chloro-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-1,7-dihydro-purin-6-one (4.0 g, 9.16 mmol), NaCN (0.67 g, 13.74 mmol), NaI (2.0 g, 9.16 mmol) and DMF (30 ml) were stirred for 48 hrs at 60° C. Reaction mixture was cooled to 20-25° C. and water was added and solid filtered off. The crude product was purified by column chromatography using silica gel (100-200 mesh) and 2 to 4% methanol in DCM as an eluent to obtain 6-Oxo-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-6,7-dihydro-1H-purine-2-carbonitrile (2.6 g, 67%) as an off white solid.

Workup

  1. customReaction mixture
  2. temperaturewas cooled to 20-25° C.
  3. filtrationsolid filtered off
  4. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-aca8081fe6f84810a916ea3504a7173b
Source dataset
uspto-grants-2014_10
Patent number
US08859566B2

Reaction notes

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