Aluminium lithium hydride → HCID 178476559, compound

HRID 432209Notes

Reaction equation

HRID 432209 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([OH:8])(=[O:7])[CH3:6].[NH2:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]2[N:16]([C@H:35]3[CH2:40][CH2:39][C@@H:38]([N:41]4[CH2:46][CH2:45][N:44]([CH3:47])[CH2:43][CH2:42]4)[CH2:37][CH2:36]3)[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26](=O)[CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:21][CH:20]=3)[C:11]=12.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]([OH:4])(=[O:3])[CH3:2].[C:5]([OH:8])(=[O:7])[CH3:6].[CH3:47][N:44]1[CH2:43][CH2:42][N:41]([C@@H:38]2[CH2:39][CH2:40][C@H:35]([N:16]3[C:12]4=[N:13][CH:14]=[N:15][C:10]([NH2:9])=[C:11]4[C:18]([C:19]4[CH:20]=[CH:21][C:22]([NH:25][CH2:26][CH2:27][C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=5)=[CH:23][CH:24]=4)=[N:17]3)[CH2:36][CH2:37]2)[CH2:46][CH2:45]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178476563HCID 178476563, compound

Product 1

HCID 178476559HCID 178476559, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Cis-N1-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-2-phenylacetamide diacetate (0.200 g, 0.00031 mol) was suspended in anhydrous tetrahydrofuran (15 mL), the suspension was cooled to 0° C. and lithium aluminum hydride (0.177 g, 0.00416 mol) was added at once. The resulting mixture was warmed up to ambient temperature and stirred under an atmosphere of nitrogen for 18 hours. It was quenched by dropwise addition of water, the solvents were removed under reduced pressure and the residue purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min) to yield cis-1-[4-(4-methylpiperazino)cyclohexyl]-3-[4-(phenethylamino)phenyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine diacetate (0.039 g, 0.0000619 mol) as a white solid.

Workup

  1. temperatureThe resulting mixture was warmed up to ambient temperature
  2. customIt was quenched by dropwise addition of water
  3. customthe solvents were removed under reduced pressure
  4. customthe residue purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min)

Sources & evidence

ORD record
ord-dce65495aeb147b29bdeb818a8c19e2d
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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