m-Chloroperbenzoic acid → 2-allyl-6-{[3-hydroxymethyl-4-(4-methylpiperazin-1-yl)phenyl]amino}-1-pyridin-2-yl-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one

HRID 545246Notes

Reaction equation

HRID 545246 reaction equation
ClC1C=CC=C(C(OO)=O)C=1.[CH2:12]([N:15]1[C:23](=[O:24])[C:22]2[C:17](=[N:18][C:19](SC)=[N:20][CH:21]=2)[N:16]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)[CH:13]=[CH2:14].C(N(CC)C(C)C)(C)C.[NH2:42][C:43]1[CH:44]=[CH:45][C:46]([N:51]2[CH2:56][CH2:55][N:54]([CH3:57])[CH2:53][CH2:52]2)=[C:47]([CH2:49][OH:50])[CH:48]=1.C(=O)([O-])O.[Na+]>O1CCCC1.C1(C)C=CC=CC=1>[CH2:12]([N:15]1[C:23](=[O:24])[C:22]2[C:17](=[N:18][C:19]([NH:42][C:43]3[CH:44]=[CH:45][C:46]([N:51]4[CH2:52][CH2:53][N:54]([CH3:57])[CH2:55][CH2:56]4)=[C:47]([CH2:49][OH:50])[CH:48]=3)=[N:20][CH:21]=2)[N:16]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)[CH:13]=[CH2:14]

Participants

8

Reactant 5

HCID 70297m-Chloroperbenzoic acidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 36995517(5-Amino-2-(4-methylpiperazin-1-yl)phenyl)methanolHCID 671712462-allyl-6-(methylthio)-1-pyridin-2-yl-3H-pyrazolo[3,4-d]pyrimidin-3-one

Product 1

HCID 248577532-allyl-6-{[3-hydroxymethyl-4-(4-methylpiperazin-1-yl)phenyl]amino}-1-pyridin-2-yl-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-oneYield 66.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

796 mg of m-chloroperbenzoic acid (>65%) was added to toluene (20 mL) solution of 898 mg of 2-allyl-6-(methylthio)-1-pyridin-2-yl-3H-pyrazolo[3,4-d]pyrimidin-3one, and stirred for 30 minutes. 1.60 mL of N,N-diisopropylethylamine, 800 mg of [5-amino-2-(4-methylpiperazin-1-yl)phenyl]methanol and 10 mL of tetrahydrofuran were added to the reaction liquid, and stirred overnight. Aqueous saturated sodium hydrogencarbonate solution was added to the reaction liquid, and extracted with a mixed solution of chloroform/isopropanol (80/20). This was dried with anhydrous magnesium sulfate, the solvent was evaporated away, and the residue was purified through basic silica gel column chromatography (hexane/ethyl acetate=50/50 to 0/100). The resulting crystal was recrystallized from ethanol to obtain 941 mg of the entitled compound as a white crystal.

Workup

  1. stirringstirred overnight
  2. extractionextracted with a mixed solution of chloroform/isopropanol (80/20)
  3. dry with materialThis was dried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated away
  5. customthe residue was purified through basic silica gel column chromatography (hexane/ethyl acetate=50/50 to 0/100)
  6. customThe resulting crystal was recrystallized from ethanol

Sources & evidence

ORD record
ord-50c77c6f605f4d8496e9e875216aa2e1
Source dataset
uspto-grants-2011_05
Patent number
US07935708B2

Reaction notes

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