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

HRID 1429717Notes

Reaction equation

HRID 1429717 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 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
67.5 °C

Procedure

A mixture of 2-Chloro-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-1,7-dihydro-purin-6-one (0.1 g, 0.23 mmol), NaCN (0.016 g, 0.35 mmol), NaI (0.069 g, 0.46 mmol) and DMF (2 ml) were stirred for 48 h at 65-70° C. Reaction mixture was cooled to 20-25° C. and water was added. Solid material was separated. It was filtered off and washed with water. The product was dried under vacuum to obtain 6-Oxo-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-6,7-dihydro-1H-purine-2-carbonitrile (0.075 g, 77%) as an off white solid.

Workup

  1. customReaction mixture
  2. temperaturewas cooled to 20-25° C.
  3. customSolid material was separated
  4. filtrationIt was filtered off
  5. washwashed with water
  6. customThe product was dried under vacuum

Sources & evidence

ORD record
ord-2d865cbdc3164b57aec3a1155ab229eb
Source dataset
uspto-grants-2015_01
Patent number
US08940751B2

Reaction notes

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