Aluminium lithium hydride → HCID 118159565, compound

HRID 628274Notes

Reaction equation

[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[C:12]([CH3:14])[N:11]([CH2:15][C:16]4[CH:17]=[C:18]([CH:23]=[CH:24][CH:25]=4)[C:19](OC)=[O:20])[C:8]=3[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[C:12]([CH3:14])[N:11]([CH2:15][C:16]4[CH:17]=[C:18]([CH2:19][OH:20])[CH:23]=[CH:24][CH:25]=4)[C:8]=3[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of methyl 3-[(1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridin-6-yl)methyl]benzoate (0.96 g, 2.7 mmol, prepared as in Example 26, Step 1) in THF (90 mL) at 0° C. was added dropwise a solution of 1.0 M LiAlH4 in THF (4.0 mL, 4.0 mmol, Aldrich). After 20 minutes, additional 1.0 M LiAlH4 in THF (1.3 mL, 1.3 mmol) was added. After 20 additional minutes, the reaction was quenched by the dropwise addition of water. The reaction was cooled to 0° C. and excess Rochelle's salt was added and stirred until the solution was clear. Sodium sulfate was then added, the mixture was filtered through celite and the solvent was removed in vacuo. Flash chromatography, eluting with a gradient from 0-10% MeOH in DCM afforded product as a light yellow solid (0.61 g, 74%).

Workup

customAfter 20 additional minutes, the reaction was quenched by the dropwise addition of water
additionexcess Rochelle's salt was added
additionSodium sulfate was then added
filtrationthe mixture was filtered through celite
customthe solvent was removed in vacuo
washFlash chromatography, eluting with a gradient from 0-10% MeOH in DCM afforded product as a light yellow solid (0.61 g, 74%)

Sources & evidence

ORD record: ord-c7405e4074344c8fa3bf25435ea68c03
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309246B2

Reaction notes

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