Aluminium lithium hydride → HCID 136623188, compound

HRID 2279110Notes

Reaction equation

[CH2:1]([N:8]1[C@H:13]([CH3:14])[CH2:12][N:11]([C:15]([C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[N:20]=[C:19]3[N:30]([CH:34]4[CH2:39][CH2:38][CH2:37][CH2:36][O:35]4)[N:31]=[C:32]([CH3:33])[C:18]=23)=O)[C@@H:10]([CH3:40])[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[C@H:13]([CH3:14])[CH2:12][N:11]([CH2:15][C:17]2[CH:22]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[N:20]=[C:19]3[N:30]([CH:34]4[CH2:39][CH2:38][CH2:37][CH2:36][O:35]4)[N:31]=[C:32]([CH3:33])[C:18]=23)[C@@H:10]([CH3:40])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

600 mg of ((2S,5R)-4-benzyl-2,5-dimethyl-piperazin-1-yl)-[6-(4-hydroxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-4-yl]-methanone were dissolved in 10 ml of THF. Under Argon-atmosphere, 1.1 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 5 ml EtOAc and 5 ml water. The mixture was filtered over celite by suction and washed with EtOAc. The solvents were removed in vacuo and 500 mg (86%) of the title compound were obtained and used without further purification.

Workup

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

Sources & evidence

ORD record: ord-9187f319fd7d488f9be8647baa7bb7aa
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133181B2

Reaction notes

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