Aluminium lithium hydride → [4-(Ethylamino)-6-methyl-2-(methylthio)pyrimidin-5-yl]methanol

HRID 1666252Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([NH:9][C:10]1[C:15]([C:16](OCC)=[O:17])=[C:14]([CH3:21])[N:13]=[C:12]([S:22][CH3:23])[N:11]=1)[CH3:8]>C1COCC1>[CH2:7]([NH:9][C:10]1[C:15]([CH2:16][OH:17])=[C:14]([CH3:21])[N:13]=[C:12]([S:22][CH3:23])[N:11]=1)[CH3:8]

Participants

Conditions

Temperature: 0 °C

Procedure

To a lithium aluminum hydride solution (LAH, 1.0 M solution in THF, Aldrich, 450 mL) was added a solution of ethyl 4-(ethylamino)-6-methyl-2-(methylthio)pyrimidine-5-carboxylate (57 g) in THF (1000 mL). The reaction mixture was stirred overnight. After cooling to 0° C., the reaction mixture was cautiously quenched with a 1:9 mixture of H2O/THF until gas evolution has ceased, then diluted with H2O (500 mL) and stirred well for 2 h. The resulting slurry was extracted with ethylacetate several times. The aqueous layer was then filtered through Celite and washed with ethylacetate again. The combined organic layers were washed with brine, dried and concentrated under reduced pressure to give 41.0 g (85% yield) of [4-(ethylamino)-6-methyl-2-(methylthio)pyrimidin-5-yl]methanol as a light yellow crystal, which was used without purification in the next step.

Workup

customthe reaction mixture was cautiously quenched with a 1:9 mixture of H2O/THF until gas evolution
additiondiluted with H2O (500 mL)
stirringstirred well for 2 h
extractionThe resulting slurry was extracted with ethylacetate several times
filtrationThe aqueous layer was then filtered through Celite
washwashed with ethylacetate again
washThe combined organic layers were washed with brine
customdried
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-792c36fcdafe419dad1a5e2d0e963d85
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044062B2

Reaction notes

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