Dimethylformamide → Methyl 6-(2-butenylamino)-3-[(4,6-dimethoxypyrimidin-2-yl)oxy]picolinate

HRID 1653638노트

반응식

HRID 1653638 반응식
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([O:12][C:13]2[N:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[N:14]=2)=[CH:4][CH:3]=1.[CH2:23](Br)[CH:24]=[CH:25][CH3:26].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:23]([NH:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[C:5]([O:12][C:13]2[N:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[N:14]=2)=[CH:4][CH:3]=1)[CH:24]=[CH:25][CH3:26]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1224142-Butene, 1-bromo-HCID 15239974Methyl 3-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-aminopicolinate

생성물 1

HCID 54239403Methyl 6-(2-butenylamino)-3-[(4,6-dimethoxypyrimidin-2-yl)oxy]picolinate수율 36.6%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

3.0 g (9.8 mmol) of methyl 6-amino-3-[(4,6-dimethoxypyrimidin-2-yl)oxy]picolinate, 1.5 g (10.8 mmol) of 2-butenyl bromide and 1.6 g (11.8 mmol) of potassium carbonate were added to 10 ml of DMF, and the mixture was stirred at 100° C. for one hour. After completion of the reaction, the reaction mixture was poured into water, then extracted with ethyl acetate, dried and concentrated. Then, the obtained residue was purified by column chromatography and crystallized to obtain a solid, which was washed with diisopropyl ether to obtain the desired product as colorless prism crystals.

후처리

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. customdried
  4. concentrationconcentrated
  5. customThen, the obtained residue was purified by column chromatography
  6. customcrystallized
  7. customto obtain a solid, which
  8. washwas washed with diisopropyl ether

출처 및 근거

ORD 기록
ord-ef863ee8d60d4f1bb065c2d1e357b5a2
출처 데이터셋
uspto-grants-1995_04
특허 번호
US05403816

반응 노트

불러오는 중…