Aluminium lithium hydride → 4-(4-Benzyl-2,2-dimethyl-piperazin-1-ylmethyl)-6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine

HRID 2279092Notes

Reaction equation

HRID 2279092 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:24][C:23]=3[F:36])[N:19]=[C:18]3[N:37]([CH:41]4[CH2:46][CH2:45][CH2:44][CH2:43][O:42]4)[N:38]=[C:39]([CH3:40])[C:17]=23)=O)[C:10]([CH3:48])([CH3:47])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:16]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:24][C:23]=3[F:36])[N:19]=[C:18]3[N:37]([CH:41]4[CH2:46][CH2:45][CH2:44][CH2:43][O:42]4)[N:38]=[C:39]([CH3:40])[C:17]=23)[C:10]([CH3:48])([CH3:47])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90013862(4-Benzyl-2,2-dimethyl-piperazin-1-yl)-[6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanone

Product 1

HCID 900140774-(4-Benzyl-2,2-dimethyl-piperazin-1-ylmethyl)-6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridineYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

410 mg of (4-benzyl-2,2-dimethyl-piperazin-1-yl)-[6-(4-benzyloxy-2-fluoro-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanone were dissolved in 8 ml of THF. Under Argon-atmosphere, 0.53 ml of lithium aluminium hydride (2.4M in THF) was added and the reaction was heated to reflux for 2 h. The reaction was then cooled to 0° C., and quenched by the addition of 3 ml EtOAc and 3 ml water. The mixture was filtered over celite by suction and washed with EtOAc. The solvents were removed in vacuo and 200 mg (50%) of the title compound were obtained and used without further purification.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 2 h
  3. customquenched by the addition of 3 ml EtOAc and 3 ml water
  4. filtrationThe mixture was filtered over celite by suction
  5. washwashed with EtOAc
  6. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-fdc850b6ccc540abacfbe1f2604fa0db
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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