2-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)- → 2,6-dimethyl-3-(2-(4-morpholinophenyl)thiazol-5-yl)pyrimidin-4(3H)-one

HRID 56119ノート

反応式

HRID 56119 の反応式
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[S:14][C:15]([NH2:18])=[CH:16][N:17]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C[Al](C)C.[NH:23](/[C:27](/[CH3:33])=[CH:28]\[C:29](OC)=[O:30])[C:24]([CH3:26])=O>C(Cl)Cl>[CH3:26][C:24]1[N:18]([C:15]2[S:14][C:13]([C:10]3[CH:9]=[CH:8][C:7]([N:4]4[CH2:5][CH2:6][O:1][CH2:2][CH2:3]4)=[CH:12][CH:11]=3)=[N:17][CH:16]=2)[C:29](=[O:30])[CH:28]=[C:27]([CH3:33])[N:23]=1

参加物

5

反応物 3

HCID 57053602-Butenoic acid, 3-(acetylamino)-, methyl ester, (2Z)-HCID 16682925TrimethylaluminumHCID 900229082-(4-Morpholinophenyl)thiazol-5-amine

生成物 1

HCID 729485772,6-dimethyl-3-(2-(4-morpholinophenyl)thiazol-5-yl)pyrimidin-4(3H)-one収率 7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-(4-morpholinophenyl)thiazol-5-amine (0.20 g, 0.77 mmol) in CH2Cl2 (20 mL) was added trimethylaluminum (2.3 mL, 4.6 mmol, 2 M in toluene) dropwise at rt. The reaction mixture was stirred at rt for 1 h, followed by the addition of a solution of methyl 3-acetaminocrotonate (132 mg, 0.84 mmol) in anhydrous CH2Cl2 (5 mL). The reaction mixture was stirred at rt overnight, then quenched with saturated NH4Cl aqueous solution and extracted with CH2Cl2 (50 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by preparative TLC to give the title compound as a pale yellow solid (20 mg, 7%). The compound was characterized by the following spectroscopic data:

後処理

  1. stirringThe reaction mixture was stirred at rt overnight
  2. customquenched with saturated NH4Cl aqueous solution
  3. extractionextracted with CH2Cl2 (50 mL×3)
  4. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative TLC

出典と根拠

ORDレコード
ord-0893ecf08c374e40a862e51ea95e6d11
出典データセット
uspto-grants-2016_09
特許番号
US09434695B2

反応ノート

読み込み中…