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

HRID 426282노트

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HRID 426282 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-a9ab288c0278407bbf226a81c73ac7db
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106064B2

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