N-bromobutanimide → 5-Bromo-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine

HRID 1355818ノート

反応式

HRID 1355818 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[C:10]([S:12][CH3:13])[N:9]=[C:8]([NH2:14])[N:7]=1.[Br:15]N1C(=O)CCC1=O>C(O)(=O)C>[Br:15][C:11]1[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)=[N:7][C:8]([NH2:14])=[N:9][C:10]=1[S:12][CH3:13]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 185076524-Furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine

生成物 1

HCID 185075225-Bromo-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine収率 34.2%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a stirred solution of 197 mg (0.95 mmol) 4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine in 15 ml acetic acid was added 178 mg (1.00 mmol) N-bromosuccinimide and stirring continued at room temperature for 48 h. The reaction mixture was then concentrated in vacuo and the residue partitioned between ether and water. The organic phase was dried over, sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate/hexane 1/2) followed by trituration in ether/hexane then afforded 93 mg (34%) 5-bromo-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine as a yellow crystalline solid. EI-MS m/e (%): 287 (M{81Br}+, 44), 285 (M{79Br}+, 42), 206 ([M—Br]+, 100).

後処理

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue partitioned between ether and water
  3. dry with materialThe organic phase was dried over, sodium sulfate
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-fa080306a71b4f81bd3b312fd8af2031
出典データセット
uspto-grants-2003_07
特許番号
US06586441B2

反応ノート

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