Dimethylformamide → 3-[2-(Methylthio)-4-pyrimidinyl]-2-(3-nitrophenyl)-5-[(phenylmethyl)oxy]-pyrazolo[1,5-a]pyridine

HRID 1159945노트

반응식

HRID 1159945 반응식
CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:14][N+:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:17][CH:16]=1.[CH3:29][S:30][C:31]1[N:36]=[C:35]([C:37]#[C:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([N+:45]([O-:47])=[O:46])[CH:40]=2)[CH:34]=[CH:33][N:32]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>O>[CH3:29][S:30][C:31]1[N:36]=[C:35]([C:37]2[C:38]([C:39]3[CH:44]=[CH:43][CH:42]=[C:41]([N+:45]([O-:47])=[O:46])[CH:40]=3)=[N:14][N:15]3[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[CH:19][C:20]=23)[CH:34]=[CH:33][N:32]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 595114132-(Methylthio)-4-[(3-nitrophenyl)ethynyl]pyrimidineHCID 866187801-Amino-4-[(phenylmethyl)oxy]pyridinium 2,4,6-trimethylbenzenesulfonate

생성물 1

HCID 595138483-[2-(Methylthio)-4-pyrimidinyl]-2-(3-nitrophenyl)-5-[(phenylmethyl)oxy]-pyrazolo[1,5-a]pyridine수율 10.6%

시약·촉매·용매 1

HCID 962Water용매

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온도
0 °C

실험 절차

A solution of 1-amino-4-[(phenylmethyl)oxy]pyridinium 2,4,6-trimethylbenzenesulfonate (13.8 mmol; crude) and 2-(methylthio)-4-[(3-nitrophenyl)ethynyl]pyrimidine (6.30 g, 9.22 mmol) in dry-DMF (70 mL) was cooled to 0° C. Aq. K2CO3 (2.75 mL, 18.4 mmol) was added. The mixture was stirred at rt overnight. The reaction mixture was poured into water and extracted with EtOAc. The organic phase was combined, washed with brine, and dried (MgSO4). The solvent was evaporated under reduced pressure. Chromatography on silica gel eluting with hexane/EtOAc gradient (15-50% EtOAc) gave yellow solid (460 mg).

후처리

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-64f5b57c16704a7a803a428f55c9a617
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812022B2

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