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

HRID 886786ノート

反応式

HRID 886786 の反応式
[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]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 57606964Ethyl 4-(ethylamino)-6-methyl-2-(methylthio)pyrimidine-5-carboxylate

生成物 1

HCID 57606985[4-(Ethylamino)-6-methyl-2-(methylthio)pyrimidin-5-yl]methanol収率 86.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-7086f5572be64f629b9568301ff82a1f
出典データセット
uspto-grants-2012_08
特許番号
US08247408B2

反応ノート

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