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

HRID 2284398노트

반응식

HRID 2284398 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>ClCCl>[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, 1.178 mmol) in dichloromethane (15 mL), morpholine (0.566 mL, 0.0066 mol) was slowly added and the reaction was continued for 20 minutes. The reaction mixture was diluted with dichloromethane and washed with water. The organic layer was dried over sodium sulphate and evaporated to provide crude solid. The crude material was purified using column chromatography (60-120 silica gel, 30% ethyl acetate in hexane) to provide 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: 345.0; Observed mass [M+H]+: 347.8 (RT: 1.70 min).

후처리

  1. washwashed with water
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. customevaporated
  4. customto provide crude solid
  5. customThe crude material was purified

출처 및 근거

ORD 기록
ord-40fd101792e74b128f2455dd0a57971f
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145411B2

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