Aluminium lithium hydride → [4-(Ethylamino)-6-methyl-2-(methylthio)pyrimidin-5-yl]methanol
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-7086f5572be64f629b9568301ff82a1f
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08247408B2
Reaction notes
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