Potassium Carbonate → 4-(1H-pyrrolo[3,2-c]pyridin-3-yl)-N-o-tolylpyrimidin-2-amine

HRID 1042552노트

반응식

HRID 1042552 반응식
C(=O)([O-])[O-].[K+].[K+].C[Si](C)(C)[C:9]#[C:10][C:11]([C:13]1[C:17]2[CH:18]=[N:19][CH:20]=[CH:21][C:16]=2[N:15](C(OC(C)(C)C)=O)[CH:14]=1)=O.[N+]([O-])([O-])=O.[CH3:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[NH:42][C:43]([NH2:45])=[NH2+:44]>COCCO>[NH:15]1[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[C:13]([C:11]2[CH:10]=[CH:9][N:45]=[C:43]([NH:42][C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=3[CH3:35])[N:44]=2)=[CH:14]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 58230463Tert-butyl 3-(3-trimethylsilylpropynoyl)pyrrolo[3,2-c]pyridine-1-carboxylateHCID 178424377HCID 178424377, 화합물

생성물 1

HCID 249923864-(1H-pyrrolo[3,2-c]pyridin-3-yl)-N-o-tolylpyrimidin-2-amine

시약·촉매·용매 1

HCID 80192-Methoxyethanol용매

실험 절차

173 mg (1.25 mmol) of potassium carbonate are added to a solution of 171 mg (0.50 mmol) of tert-butyl 3-(3-trimethylsilylpropynoyl)pyrrolo[3,2-c]pyridine-1-carboxylate and 265 mg (1.25 mmol) of 2-methylphenylguanidinium nitrate (prepared by the method of J. L. Hughes et al., J. Med. Chem. 1975, 18, 1077-1088) in 2.5 ml of ethylene glycol monomethyl ether, and the mixture is heated at the boil for 18 hours. After cooling, the reaction mixture is partitioned between water and dichloromethane. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent, giving [4-(1H-pyrrolo-[3,2-c]pyridin-3-yl)pyrimidin-2-yl]-o-tolyl-amine (“A6”) as beige crystals; ESI 303;

후처리

  1. customprepared by the method of J
  2. temperatureAfter cooling
  3. customthe reaction mixture is partitioned between water and dichloromethane
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated
  6. customThe residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent

출처 및 근거

ORD 기록
ord-14a87e84c53744d3abdcdf1b6d1689a6
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557977B2

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