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

HRID 510141Notes

Reaction equation

HRID 510141 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:14](=[O:15])[N:13]([CH2:16][CH:17]2[CH2:20][CH2:19][O:18]2)[C:12]2[C:7]1=[N:8][C:9]([C:21]1[C:29]3[C:24](=[N:25][CH:26]=[CH:27][CH:28]=3)[N:23]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[F:37])[N:22]=1)=[N:10][CH:11]=2.C([SiH](CC)CC)C.O.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O.C(OCC)(=O)C>[F:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[CH2:30][N:23]1[C:24]2=[N:25][CH:26]=[CH:27][CH:28]=[C:29]2[C:21]([C:9]2[N:8]=[C:7]3[C:12]([N:13]([CH2:16][CH:17]4[CH2:20][CH2:19][O:18]4)[C:14](=[O:15])[NH:6]3)=[CH:11][N:10]=2)=[N:22]1

Participants

7

Reactant 4

HCID 962WaterHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 666140889-(2,4-Dimethoxybenzyl)-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7-(oxetan-2-ylmethyl)-7,9-dihydro-8H-purin-8-one

Product 1

HCID 666135192-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7-(oxetan-2-ylmethyl)-7,9-dihydro-8H-purin-8-oneYield 48.9%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

476 mg (0.82 mmol) of the compound from example 86A were dissolved in 15 ml of trifluoroacetic acid, 953 mg (8.20 mmol) of triethylsilane were added and the mixture was heated to reflux for 18 h. The reaction mixture was admixed with water and ethyl acetate, and neutralized with saturated aqueous sodium hydrogencarbonate solution. The organic phase was dried over sodium sulfate and concentrated on a rotary evaporator. The residue was dried under high vacuum, and purified by means of preparative HPLC (eluent: methanol/water with 0.1% trifluoroacetic acid, gradient 30:70→90:10). 173 mg of the title compound were obtained (49% of theory).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 h
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated on a rotary evaporator
  5. customThe residue was dried under high vacuum
  6. custompurified by means of preparative HPLC (eluent: methanol/water with 0.1% trifluoroacetic acid, gradient 30:70→90:10)

Sources & evidence

ORD record
ord-24fa3137c4c1484f8f0c0646a0926f87
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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