Potassium Carbonate → {2-[6-(4-chloro-phenylamino)-9-methyl-9H-purin-2-yl]-5-methyl-2H-pyrazol-3-yl}-methanol

HRID 1809276Notes

Reaction equation

HRID 1809276 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:17]=[C:16]([N:18]3[C:22]([CH2:23][O:24]C4CCCCO4)=[CH:21][C:20]([CH3:31])=[N:19]3)[N:15]=[C:14]3[C:10]=2[N:11]=[CH:12][N:13]3[CH3:32])=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:17]=[C:16]([N:18]3[C:22]([CH2:23][OH:24])=[CH:21][C:20]([CH3:31])=[N:19]3)[N:15]=[C:14]3[C:10]=2[N:11]=[CH:12][N:13]3[CH3:32])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 59322258(4-Chloro-phenyl)-{9-methyl-2-[3-methyl-5-(tetrahydro-pyran-2-yloxymethyl)pyrazol-1-yl]-9H-purin-6-yl}-amine

Product 1

HCID 25017123{2-[6-(4-chloro-phenylamino)-9-methyl-9H-purin-2-yl]-5-methyl-2H-pyrazol-3-yl}-methanolYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(4-Chloro-phenyl)-{9-methyl-2-[3-methyl-5-(tetrahydro-pyran-2-yloxymethyl)-pyrazol-1-yl]-9H-purin-6-yl}-amine (240 mg, 0.53 mmol) was dissolved in methanol (30 mL). p-Toluenesulfonic acid monohydrate (90 mg, 0.48 mmol) was added and the reaction mixture was heated to reflux for 24 hours. Upon cooling a white crystalline compound was formed. The crystals were stirred with potassium carbonate (2 M), collected by filtration, washed with water and dried to give {2-[6-(4-chloro-phenyl-amino)-9-methyl-9H-purin-2-yl]-5-methyl-2H-pyrazol-3-yl}-methanol (60 mg, 31%)

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 24 hours
  3. temperatureUpon cooling a white crystalline compound
  4. customwas formed
  5. filtrationcollected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-c8058db107b841a7b34c522b8daa95da
Source dataset
uspto-grants-2013_01
Patent number
US08362024B2

Reaction notes

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