Aluminium lithium hydride → {4-[4-(4-Amino-butyl)-phenyl]-pyrimidin-2-yl}-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine

HRID 1435008Notes

Reaction equation

[CH3:1][C:2]1([CH3:28])[CH2:7][CH:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][C:24]#[N:25])=[CH:17][CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH2:5][C:4]([CH3:27])([CH3:26])[NH:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:13]2[CH:12]=[CH:11][N:10]=[C:9]([NH:8][CH:6]3[CH2:5][C:4]([CH3:27])([CH3:26])[NH:3][C:2]([CH3:28])([CH3:1])[CH2:7]3)[N:14]=2)=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-{4-[2-(2,2,6,6-tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-phenyl}-butyronitrile (Example 192) (37 mg, 0.10 mmol) in 2 ml THF was added LAH (1 M in THF, 294 μl, 0.294 mmol). The reaction mixture was stirred at 60° C. for 2 hours. The mixture was quenched with 0.5 ml aqueous sodium sulfate, followed by 2N-NaOH (pH 11). Extraction with EtOAc and purification using preparative HPLC gave the title compound. Yield: 16 mg (43%).

Workup

customThe mixture was quenched with 0.5 ml aqueous sodium sulfate
extractionExtraction
customwith EtOAc and purification

Sources & evidence

ORD record: ord-cbaab532ee9d4f8e9e7ff0ed642dbd46
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615562B2

Reaction notes

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