Ammonium Hydroxide → HCID 178437842, compound

HRID 1597865Notes

Reaction equation

HRID 1597865 reaction equation
[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([N:22]5[CH:26]=[CH:25][N:24]=[CH:23]5)[CH:17]=4)=[N:13][C:14](N)=[C:9]3[C:8]([CH2:27][CH3:28])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.N([O-])=[O:30].[Na+].[NH4+].[OH-]>O.OS(O)(=O)=O.O>[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([N:22]5[CH:26]=[CH:25][N:24]=[CH:23]5)[CH:17]=4)=[N:13][C:14](=[O:30])[C:9]3=[C:8]([CH2:27][CH3:28])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 21846079HCID 21846079, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178437842HCID 178437842, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21910475Sulfuric acid hydrate (1:1)Solvent

Procedure

To a solution of 1-cyclopentyl-3-ethyl-6-[3-(1-imidazolyl)phenyl]pyrazolo[3,4-d]pyrimidin-4-amine (6.24 g, 16.7 mmol), in 45 ml of H2O/H2SO4 (1:1) in an EtOH/ice bath was added sodium nitrite (5.77 g) in water (5 ml) in small portions over 1.5 hours. The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was poured into ice/water (500 ml) and neutralized with NH4OH to afford a yellow precipitate which was collected by filtration, washed with water, then ether. The product was recrystallized from EtOAc/MeOH, then MeOH to afford 1-cyclopentyl-3-ethyl-6-[3-(1-imidazolyl)phenyl]pyrazolo-[3,4-d]pyrimidin-4-one, m.p. 264°-265° C.

Workup

  1. customto afford a yellow precipitate which
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customThe product was recrystallized from EtOAc/MeOH

Sources & evidence

ORD record
ord-cc736f16fc6a40fcba475c8bc51edb2e
Source dataset
uspto-grants-1998_04
Patent number
US05736548

Reaction notes

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