Water → 2-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6-methyl-7,9-dihydro-8H-purin-8-one

HRID 510123Notes

Reaction equation

HRID 510123 reaction equation
C(O)=O.[NH2:4][C:5]1[C:10]([NH:11][C:12](=O)[O:13]C)=[C:9]([CH3:16])[N:8]=[C:7]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[F:33])[N:18]=2)[N:6]=1.O>O1CCCC1>[F:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH2:26][N:19]1[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:25]2[C:17]([C:7]2[N:6]=[C:5]3[C:10]([NH:11][C:12](=[O:13])[NH:4]3)=[C:9]([CH3:16])[N:8]=2)=[N:18]1

Participants

4

Reactant 2

HCID 962WaterHCID 86720046Methyl {4-amino-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6-methylpyrimidin-5-yl}carbamate formate

Product 1

HCID 666142882-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6-methyl-7,9-dihydro-8H-purin-8-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere, 245 mg (0.60 mmol) of the compound from example 69A were initially charged in tetrahydrofuran (2.6 ml) and cooled to 0° C., and 0.90 ml (0.90 mmol) of bis(trimethylsilyl)sodium amide (1.0 M in tetrahydrofuran) was added dropwise. The mixture was stirred at 0° C. for 1 h and then at RT overnight. Subsequently, the mixture was stirred at 60° C. for 8 h. Thereafter, water was added and the reaction mixture was concentrated. The residue was extracted twice with ethyl acetate, and the collected organic phases were washed with water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. This gave 110 mg (85% purity, 41% of theory) of the title compound in solid form. A solid likewise precipitated out of the aqueous phase, which was filtered off, washed with water and dried under high vacuum. This gave a further 100 mg (44% of theory) of the title compound.

Workup

  1. customat RT
  2. customovernight
  3. stirringSubsequently, the mixture was stirred at 60° C. for 8 h
  4. concentrationthe reaction mixture was concentrated
  5. extractionThe residue was extracted twice with ethyl acetate
  6. washthe collected organic phases were washed with water and saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customA solid likewise precipitated out of the aqueous phase, which
  11. filtrationwas filtered off
  12. washwashed with water
  13. customdried under high vacuum

Sources & evidence

ORD record
ord-5208600f810347839061c45968f0be15
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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