Water → HCID 57531498, compound

HRID 1091932Notes

Reaction equation

HRID 1091932 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH3:16])[C:10]=1[C:17]1[N:22]=[C:21]([N:23]2[CH2:28][CH2:27][C:26]([O:31][Si](C)(C)C)([C:29]#[N:30])[CH2:25][CH2:24]2)[C:20]([CH2:36][N:37]([CH3:48])[CH:38]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH2:41][CH2:40][CH2:39]2)=[C:19]([CH3:49])[N:18]=1)[CH3:8].O.[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.CCOC(C)=O>[NH2:30][CH2:29][C:26]1([OH:31])[CH2:27][CH2:28][N:23]([C:21]2[C:20]([CH2:36][N:37]([CH3:48])[C@@H:38]3[C:47]4[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=4)[CH2:41][CH2:40][CH2:39]3)=[C:19]([CH3:49])[N:18]=[C:17]([C:10]3[C:9]([CH2:7][CH3:8])=[CH:14][CH:13]=[CH:12][C:11]=3[CH2:15][CH3:16])[N:22]=2)[CH2:24][CH2:25]1

Participants

7

Reactant 4

HCID 962Water2×HCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 66589382HCID 66589382, compound

Product 1

HCID 57531498HCID 57531498, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a flask containing LAH (132 mg, 3.0 eq., 3.18 mmol) in anhydrous THF (20 mL) is added 1-(2-(2,6-diethyl-phenyl)-6-methyl-5-{[methyl-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amino]-methyl}-pyrimidin-4-yl)-4-trimethylsilanyloxy-piperidine-4-carbonitrile 12 (0.63 g, 1.06 mmol) as a solution in THF (5 mL) over 10 min. The reaction is refluxed overnight. Following cooling to 0° C., water (0.132 mL) NaOH (15%, 0.132 mL) and water (0.396 mL) are added successively, followed by addition of EtOAc (100 mL) and MgSO4 (100 mg). The suspension is filtered through celite and the celite bed is washed with 20:1 EtOAc:MeOH (2×100 mL). Concentration affords the title compound as an off-white solid. [mass expected (527.74); mass found (527.27)].

Workup

  1. temperatureThe reaction is refluxed overnight
  2. filtrationThe suspension is filtered through celite
  3. washthe celite bed is washed with 20:1 EtOAc
  4. concentrationConcentration

Sources & evidence

ORD record
ord-3d416df3cb2040809af5382118dd7186
Source dataset
uspto-grants-2012_03
Patent number
US08129395B2

Reaction notes

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