Phosphorus oxychloride → Ethyl 4-chloro-8-fluoroquinazoline-2-carboxylate

HRID 625805노트

반응식

HRID 625805 반응식
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:8]=[C:7]2O.O=P(Cl)(Cl)[Cl:20]>>[Cl:20][C:7]1[C:6]2[C:11](=[C:2]([F:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:8]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 178470310HCID 178470310, 화합물

생성물 1

HCID 86649064Ethyl 4-chloro-8-fluoroquinazoline-2-carboxylate수율 65%

실험 절차

A mixture of ethyl 8-fluoro-4-hydroxyquinazoline-2-carboxylate (530 mg, 2.2 mmol) and POCl3 (3 mL) was heated under reflux for 5 h. The mixture was concentrated under reduced pressure, and then toluene was twice added and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 0-25% EtOAc/hexanes to afford ethyl 4-chloro-8-fluoroquinazoline-2-carboxylate (365 mg, 65%). 1H NMR (300 MHz, DMSO-d6) δ 1.39 (t, J=7.1 Hz, 3H), 4.46 (q, J=7.1 Hz, 2H), 7.97-8.06 (m, 1H), 8.07-8.16 (m, 1H), 8.18-8.24 (m, 1H).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 5 h
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additiontoluene was twice added
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 0-25% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-ea527f0fc3ac4ed987652a546044d6da
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09308207B2

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