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

HRID 1355818노트

반응식

HRID 1355818 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fa080306a71b4f81bd3b312fd8af2031
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586441B2

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