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

HRID 1159945ノート

反応式

HRID 1159945 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-64f5b57c16704a7a803a428f55c9a617
出典データセット
uspto-grants-2010_10
特許番号
US07812022B2

反応ノート

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