Aluminium lithium hydride → {5-[(2-Chloro-3,5-dimethoxy-phenylamino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl}-ethyl-amine

HRID 1783550Notes

Reaction equation

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

Participants

Conditions

Temperature: 5 °C

Procedure

Into a suspension of 6.96 g (18.97 mmol) of {5-[(2-chloro-3,5-dimethoxy-phenylimino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl}-ethyl-amine in 200 mL of dry THF cooled to 5° C. was added 18.97 mL (18.97 mmol) of a 1 M solution of LAH in THF. After stirring for 1 hour, the cold reaction was quenched by sequential addition of 0.8 mL of water, 3.0 mL of 25 NaOH, and 1.7 mL of water. The reaction was filtered through Celite, the filter pad washed well with THF, and the filtrate concentrated in vacuo. The residue was dissolved in dichloromethane, added silica gel, and concentrated in vacuo. This residue was chromatographed on silica gel, eluting with hexane/ethyl acetate (2:1 v/v), giving 5.15 g (74%) of the title compound: mp 116.5-118.5° C.

Workup

customthe cold reaction
customwas quenched by sequential addition of 0.8 mL of water, 3.0 mL of 25 NaOH, and 1.7 mL of water
filtrationThe reaction was filtered through Celite
washthe filter pad washed well with THF
concentrationthe filtrate concentrated in vacuo
dissolutionThe residue was dissolved in dichloromethane
additionadded silica gel
concentrationconcentrated in vacuo
customThis residue was chromatographed on silica gel
washeluting with hexane/ethyl acetate (2:1 v/v)

Sources & evidence

ORD record: ord-b699cc9d2df54c71a416343e78e617c1
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501425B1

Reaction notes

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