Lithium iodide → (R)-4-(2-chloro-6-(iodomethyl)pyrimidin-4-yl)-3-methylmorpholine

HRID 888985ノート

反応式

HRID 888985 の反応式
CS(O[CH2:6][C:7]1[CH:12]=[C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][C@H:14]2[CH3:19])[N:10]=[C:9]([Cl:20])[N:8]=1)(=O)=O.[I-:21].[Li+]>O1CCOCC1>[Cl:20][C:9]1[N:10]=[C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][C@H:14]2[CH3:19])[CH:12]=[C:7]([CH2:6][I:21])[N:8]=1

参加物

4

反応物 2

HCID 66321Lithium iodideHCID 86651636(R)-(2-chloro-6-(3-methylmorpholino)pyrimidin-4-yl)methyl methanesulfonate

生成物 1

HCID 71584551(R)-4-(2-chloro-6-(iodomethyl)pyrimidin-4-yl)-3-methylmorpholine収率 86%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
107 °C

実験手順

(R)-(2-Chloro-6-(3-methylmorpholino)pyrimidin-4-yl)methyl methanesulfonate (80 g, 248.62 mmol) and lithium iodide (83 g, 621.54 mmol) were dissolved in dioxane (300 ml) and then heated at 107° C. for 1 hour. The reaction mixture was quenched with water (250 ml), extracted with EtOAc (3×250 ml), the organic layer was dried over MgSO4, filtered and evaporated. The residue was dissolved in DCM and Et2O was added, the mixture was passed through silica (4 inches) and eluted with Et2O. Fractions containing product were evaporated and the residue was then triturated with Et2O to give a solid which was collected by filtration and dried under vacuum to afford (R)-4-(2-chloro-6-(iodomethyl)pyrimidin-4-yl)-3-methylmorpholine (75 g, 86%); m/z: (ESI+) MH+, 354.27.

後処理

  1. customThe reaction mixture was quenched with water (250 ml)
  2. extractionextracted with EtOAc (3×250 ml)
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe residue was dissolved in DCM
  7. additionEt2O was added
  8. washeluted with Et2O
  9. additionFractions containing product
  10. customwere evaporated
  11. customthe residue was then triturated with Et2O
  12. customto give a solid which
  13. filtrationwas collected by filtration
  14. customdried under vacuum

出典と根拠

ORDレコード
ord-4c1d70b6fd8d49b0940f9e0135f4032a
出典データセット
uspto-grants-2012_08
特許番号
US08252802B2

反応ノート

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