Morpholine → 2-Chloro-4-morpholino-6-fluoro-7-bromo-quinazoline

HRID 517450노트

반응식

HRID 517450 반응식
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](Cl)=[N:7][C:8]([Cl:12])=[N:9]2)=[CH:4][C:3]=1[F:14].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[N:7][C:8]([Cl:12])=[N:9]2)=[CH:4][C:3]=1[F:14]

참가 물질

4

반응물 2

HCID 8083MorpholineHCID 866657637-Bromo-2,4-dichloro-6-fluoroquinazoline

생성물 1

HCID 866657622-Chloro-4-morpholino-6-fluoro-7-bromo-quinazoline수율 57%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To an ice cold solution of 7-bromo-2,4-dichloro-6-fluoro-quinazoline (0.35 g, 0.001178 mol) in DCM (15 mL), morpholine (0.247 mL, 2.946 mol) was slowly added and the reaction was continued for 20 min. The reaction mixture was diluted with DCM and washed with water. The organic layer was dried over sodium sulfate and evaporated to get the crude. The crude was purified using column chromatography (60-120 silica gel, 30% ethyl acetate in hexane) to get the title compound (220 mg, 57%). 1H NMR (300 MHz, DMSO-d6): δ 8.16 (d, J=6.6 Hz, 1H), 8.01 (d, J=9.6 Hz, 1H), 3.83-3.86 (m, 4H), 3.76-3.73 (m, 4H); LC-MS (ESI): Calculated mass: 344.9; Observed mass: 347.8 [M+H]+ (RT: 1.70 min).

후처리

  1. washwashed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated
  4. customto get the crude
  5. customThe crude was purified

출처 및 근거

ORD 기록
ord-5ef9f59cdf1d433b9a7bcf5255fbc2c6
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115092B2

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