Hydrochloric Acid → 4-[4-amino-3-(6-phenoxy-3-pyridyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-cyclo-hexanone

HRID 432166Notes

Reaction equation

HRID 432166 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[C:15]4=[N:16][CH:17]=[N:18][C:19]([NH2:20])=[C:14]4[C:13]([C:21]4[CH:22]=[N:23][C:24]([O:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)=[CH:25][CH:26]=4)=[N:12]3)[CH2:7][CH2:6]2)[O:4]CC1.Cl.C(=O)(O)[O-].[Na+]>CC(C)=O>[NH2:20][C:19]1[N:18]=[CH:17][N:16]=[C:15]2[N:11]([CH:8]3[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]3)[N:12]=[C:13]([C:21]3[CH:22]=[N:23][C:24]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:25][CH:26]=3)[C:14]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 223471771-(1,4-dioxaspiro[4.5]dec-8-yl)-3-(6-phenoxy-3-pyridyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 223467504-[4-amino-3-(6-phenoxy-3-pyridyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-cyclo-hexanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-(1,4-dioxaspiro[4.5]dec-8-yl)-3-(6-phenoxy-3-pyridyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (Intermediate AH) (1.00 g, 0.0022 mol) was triturated in acetone (20 mL) and 5N hydrochloric acid solution was added dropwise. The mixture was stirred at ambient temperature for 20 hours and neutralized with saturated sodium bicarbonate solution. The precipitate was collected by filtration, washed with water twice and dried to give 4-[4-amino-3-(6-phenoxy-3-pyridyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-cyclo-hexanone as an off-white solid (purity 94% (HPLC), 0.90 g, 0.0022 mol) ):

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water twice
  3. customdried

Sources & evidence

ORD record
ord-683a67a2015c4c28b255545c4f638c70
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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