Aluminium lithium hydride → HCID 178476560, compound

HRID 897500Notes

Reaction equation

HRID 897500 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:36]3[CH2:41][CH2:40][C@@H:39]([N:42]4[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]4)[CH2:38][CH2:37]3)[N:17]=[C:18]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26](=O)[CH2:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=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].[CH3:48][N:45]1[CH2:44][CH2:43][N:42]([C@@H:39]2[CH2:40][CH2:41][C@H:36]([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][CH2:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[CH:23][CH:24]=4)=[N:17]3)[CH2:37][CH2:38]2)[CH2:47][CH2:46]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178476564HCID 178476564, compound

Product 1

HCID 178476560HCID 178476560, compoundYield 34.1%

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)-3-phenylpropanamide diacetate (0.090 g, 0.000167 mol) was suspended in anhydrous tetrahydrofuran (5 mL), the suspension was cooled to 0° C. and lithium aluminum hydride (0.01 g, 0.00025 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-[(3-phenylpropyl)amino]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-4-amine diacetate (0.037 g, 0.000057 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-36ac90a8a09844219eb7839381ab3583
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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