Aluminium lithium hydride → HCID 54105947, compound

HRID 1783532Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([N:17]=[CH:18][C:19]2[C:20]([NH2:27])=[N:21][C:22]([S:25][CH3:26])=[N:23][CH:24]=2)[CH:12]=[C:13]([O:15][CH3:16])[CH:14]=1>O1CCCC1>[CH3:16][O:15][C:13]1[CH:12]=[C:11]([NH:17][CH2:18][C:19]2[C:20]([NH2:27])=[N:21][C:22]([S:25][CH3:26])=[N:23][CH:24]=2)[CH:10]=[C:9]([O:8][CH3:7])[CH:14]=1

Participants

Conditions

Temperature: 5 °C

Procedure

Into 18.2 mL (18.2 mmol) of a 1 M solution of lithium aluminum hydride (LAH) in tetrahydrofuran (THF) cooled to 5° C. was added a solution of 5.55 g (18.3 mmol) of 5-[(3,5-dimethoxy-phenylimino)-methyl]-2-methylsulfanyl-pyrimidin-4-ylamine in 94 mL of dry THF over 20 minutes. The reaction was stirred for 1.5 hours at 5° C., then quenched by slow sequential addition of 0.72 mL of water, 3.0 mL of 25% NaOH, and an additional 1.66 mL of water. The reaction mixture was filtered through Celite, and the filter pad was washed well with THF. The filtrate was concentrated to dryness in vacuo. The residue was dissolved in ethyl acetate. The ethyl acetate solution was washed three times with a solution of saturated sodium chloride, dried over magnesium sulfate, and concentrated in vacuo to give 5.10 g (91%) of the title compound.

Workup

customquenched by slow sequential addition of 0.72 mL of water, 3.0 mL of 25% NaOH
filtrationThe reaction mixture was filtered through Celite
washthe filter pad was washed well with THF
concentrationThe filtrate was concentrated to dryness in vacuo
dissolutionThe residue was dissolved in ethyl acetate
washThe ethyl acetate solution was washed three times with a solution of saturated sodium chloride
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-deb52e8a2d3b4d9fa5e2c6c955e224f1
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501425B1

Reaction notes

Loading…