Acetone → 2-(4-Chloro-2,6-dimethoxy-pyrimidin-5-yl)-propan-2-ol

HRID 426282ノート

反応式

HRID 426282 の反応式
Br[C:2]1[C:3]([Cl:12])=[N:4][C:5]([O:10][CH3:11])=[N:6][C:7]=1[O:8][CH3:9].C([Li])CCC.[CH3:18][C:19]([CH3:21])=[O:20]>C1COCC1>[Cl:12][C:3]1[C:2]([C:19]([OH:20])([CH3:21])[CH3:18])=[C:7]([O:8][CH3:9])[N:6]=[C:5]([O:10][CH3:11])[N:4]=1

参加物

5

反応物 3

HCID 180AcetoneHCID 122261955-Bromo-4-chloro-2,6-dimethoxypyrimidineHCID 178418339Butyllithium

生成物 1

HCID 237307032-(4-Chloro-2,6-dimethoxy-pyrimidin-5-yl)-propan-2-ol収率 55%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 5-Bromo-4-chloro-2,6-dimethoxy-pyrimidine (0.546 g, 2.16 mmol) in THF (22 mL) at −78° C. was added n-butyllithium (1.6 M in hexanes, 1.48 mL, 2.37 mmol) over 2 min. Reaction mixture was stirred from 45 min at −78° C., then acetone (0.31 mL, 4.32 mmol) was added. Reaction mixture was stirred for 1 h at −78° C., then quenched with saturated ammonium chloride solution and extracted with ethyl acetate. Organic layer was washed with saturated ammonium chloride solution, dried (MgSO4), concentrated and purified by flash column chromatography (silica gel, 10 to 30% ethyl acetate/hexane) to give a colorless oil (0.275 g, 55%). 1H NMR (300 MHz, CDCl3): δ 3.97 (br s, 1H), 3.92 (s, 3H), 3.82 (s, 3H), 1.54 (s, 6H). Mass spectrum: 233.0, 235.0 (M+H)+.

後処理

  1. customReaction mixture
  2. customReaction mixture
  3. stirringwas stirred for 1 h at −78° C.
  4. customquenched with saturated ammonium chloride solution
  5. extractionextracted with ethyl acetate
  6. washOrganic layer was washed with saturated ammonium chloride solution
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. custompurified by flash column chromatography (silica gel, 10 to 30% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-a9ab288c0278407bbf226a81c73ac7db
出典データセット
uspto-grants-2012_01
特許番号
US08106064B2

反応ノート

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