Aluminium lithium hydride → 2-methyl-2-(4-((9-methyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-6-morpholino-9H-purin-8-yl)methyl)piperidin-1-yl)propan-1-ol

HRID 1946016Notes

Reaction equation

[CH3:1][C:2]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[N:16]([CH3:40])[C:17]3[C:22]([N:23]=2)=[C:21]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[N:20]=[C:19]([N:30]2[C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=4[N:32]=[C:31]2[CH3:39])[N:18]=3)[CH2:10][CH2:9]1)([CH3:7])[C:3](OC)=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:7][C:2]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[N:16]([CH3:40])[C:17]3[C:22]([N:23]=2)=[C:21]([N:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)[N:20]=[C:19]([N:30]2[C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=4[N:32]=[C:31]2[CH3:39])[N:18]=3)[CH2:10][CH2:9]1)([CH3:1])[CH2:3][OH:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 2-methyl-2-(4-((9-methyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-6-morpholino-9H-purin-8-yl)methyl)piperidin-1-yl)propanoate 507 (0.10 g, 0.183 mmol) in THF (10 mL) was added a 1.0 M solution of lithium aluminum hydride in THF (0.18 mL, 0.18 mmol) at 0° C. The reaction was stirred at 0° C. for 1 hour. The reaction was then quenched by adding 2 mL of sat. NH4Cl solution. The cloudy mixture was then loaded onto an ISOLUTE® SCX-2 column. The column was first washed with MeOH prior to eluting the product by adding 2M NH3 in MeOH. The crude product was then concentrated and purified by RP-HPLC to give 509. LCMS m/z: 519.3 (MH+)

Workup

customThe reaction was then quenched
additionby adding 2 mL of sat. NH4Cl solution
washThe column was first washed with MeOH
washto eluting the product
additionby adding 2M NH3 in MeOH
concentrationThe crude product was then concentrated
custompurified by RP-HPLC

Sources & evidence

ORD record: ord-6db5b89c90604dc0afc6be685790c427
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394796B2

Reaction notes

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