Tetrahydrofuran → HCID 90014026, compound

HRID 2279141Notes

Reaction equation

HRID 2279141 reaction equation
[CH2:1]([N:8]1[C:13]([CH3:15])([CH3:14])[CH2:12][N:11]([C:16]([C:18]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:25]=3OC)[N:21]=[C:20]3[N:34]([CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][O:39]4)[N:35]=[C:36]([CH3:37])[C:19]=23)=O)[C:10]([CH3:45])([CH3:44])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.CSC.C1C[O:53][CH2:52]C1>>[CH2:1]([N:8]1[C:13]([CH3:15])([CH3:14])[CH2:12][N:11]([CH2:16][C:18]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH2:31][O:53][CH3:52])=[CH:26][CH:25]=3)[N:21]=[C:20]3[N:34]([CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][O:39]4)[N:35]=[C:36]([CH3:37])[C:19]=23)[C:10]([CH3:45])([CH3:44])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 12423031(Dimethyl sulfide)trihydroboronHCID 90014484HCID 90014484, compound

Product 1

HCID 90014026HCID 90014026, compoundYield 96%

Procedure

To a solution of 1.54 g of (4-benzyl-2,2,5,5-tetramethyl-piperazin-1-yl)-[6-(4-methoxy-methoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanone in 9 ml of dry THF 20 ml of borane-dimethylsulfide complex (1 M in DCM) was added slowly at r.t., and the reaction was heated to reflux for 12 h. The reaction was quenched by the addition of 13 ml of methanol, and the solvents were evaporated. The residue was purified by flash chromatography (silica, heptanes/ethyl acetate) yielding 1.44 g (96%) of the title compound.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 12 h
  3. customThe reaction was quenched by the addition of 13 ml of methanol
  4. customthe solvents were evaporated
  5. customThe residue was purified by flash chromatography (silica, heptanes/ethyl acetate)

Sources & evidence

ORD record
ord-981680134d764fc49c1e0e2f58e0b1c1
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

Loading…