1,2-Dimethoxyethane → 2-Methyl-5-(4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl)-phenylamine

HRID 2098719노트

반응식

HRID 2098719 반응식
Cl[C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[NH2:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][C:23]=1[CH3:24].COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH3:24][C:23]1[CH:22]=[CH:21][C:20]([C:2]2[N:3]=[C:4]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]3[S:10][CH:9]=[CH:8][C:6]=3[N:7]=2)=[CH:19][C:18]=1[NH2:17]

참가 물질

8

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2737803(3-Amino-4-methylphenyl)boronic acidHCID 202849712-Chloro-4-(morpholin-4-yl)thieno(3,2-d)pyrimidine

생성물 1

HCID 671889492-Methyl-5-(4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl)-phenylamine수율 94.4%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine 4 (772 mg), 3-amino-4-methylbenzeneboronic acid (502 mg), DME (10 mL), water (5 mL), sodium carbonate (640 mg) and PdCl2(PPh3)2 (100 mg) was heated to reflux for 16 hours. The reaction mixture was then cooled, diluted with ethyl acetate, and reduced in vacuo. The residue was purified using flash chromatography to yield 2-methyl-5-(4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl)-phenylamine (930 mg).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. temperatureThe reaction mixture was then cooled
  4. customThe residue was purified

출처 및 근거

ORD 기록
ord-512d5482deed41dcaa7faed1ace6a940
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450315B2

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