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

HRID 510142Notes

Reaction equation

HRID 510142 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:14](=[O:15])[N:13]([CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:12]2[C:7]1=[N:8][C:9]([C:24]1[C:32]3[C:27](=[N:28][CH:29]=[CH:30][CH:31]=3)[N:26]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[F:40])[N:25]=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:40][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[CH2:33][N:26]1[C:27]2=[N:28][CH:29]=[CH:30][CH:31]=[C:32]2[C:24]([C:9]2[N:8]=[C:7]3[C:12]([N:13]([CH2:16][CH2:17][N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[C:14](=[O:15])[NH:6]3)=[CH:11][N:10]=2)=[N:25]1

Participants

7

Reactant 4

HCID 962WaterHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 666348909-(2,4-Dimethoxybenzyl)-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7-[2-(morpholin-4-yl)ethyl]-7,9-dihydro-8H-purin-8-one

Product 1

HCID 666355982-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7-[2-(morpholin-4-yl)ethyl]-7,9-dihydro-8H-purin-8-oneYield 69.8%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

101 mg (0.16 mmol) of the compound from example 87A were dissolved in 10 ml of trifluoroacetic acid, 188 mg (1.62 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). 53 mg of the title compound were obtained (69% 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-99d0f2dfffc848afaea5615385c711bd
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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