Acetic Acid → 2-Chloro-4-ethyl-5-fluoropyrimidine

HRID 634235노트

반응식

HRID 634235 반응식
[Cl:1][C:2]1[N:7]=[C:6]([C:8](C)(C(OCC)=O)[C:9](OCC)=O)[C:5]([F:20])=[CH:4][N:3]=1.CC(O)=O.Cl.O>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][CH3:9])[C:5]([F:20])=[CH:4][N:3]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 962WaterHCID 86725111Diethyl 2-(2-chloro-5-fluoropyrimidin-4-yl)-2-methylmalonate

생성물 1

HCID 190749282-Chloro-4-ethyl-5-fluoropyrimidine수율 21%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

Diethyl 2-(2-chloro-5-fluoropyrimidin-4-yl)-2-methylmalonate (3.00 g, 9.85 mmol) was treated with glacial HOAc (25 mL) and 5N HCl (10 mL) and fitted with a reflux condenser and heated to 100° C. for 18 h. The reaction was cooled to RT and treated with H2O (30 mL) and DCM (45 mL) and the DCM layer separated and dried over MgSO4, filtered and concentrated. The crude residue was purified with flash chromatography (eluting with 100% DCM) affording 2-chloro-4-ethyl-5-fluoropyrimidine (328 mg, 21%) as a viscous pale yellow oil. MS (ESI, pos. ion) m/z: 161.0 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.34 (1H, s), 2.87 (2H, qd, J=7.6, 2.0 Hz), 1.29-1.37 (3H, t).

후처리

  1. customfitted with a reflux condenser
  2. temperatureThe reaction was cooled to RT
  3. customthe DCM layer separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified with flash chromatography (eluting with 100% DCM)

출처 및 근거

ORD 기록
ord-96c5fb475b344b1ba0e448a7f82a6f8b
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321756B2

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