Butyl iodide → 6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-vinyl-pyrimidine-4-carboxylic acid butyl ester

HRID 2386152

반응식

HRID 2386152 반응식
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH3:16])[C:9]=2[F:17])[N:5]=[C:4]([C:18]([OH:20])=[O:19])[C:3]=1[CH:21]=[CH2:22].I[CH2:24][CH2:25][CH2:26][CH3:27].C(=O)([O-])[O-].[Li+].[Li+]>CN(C=O)C>[CH2:24]([O:19][C:18]([C:4]1[C:3]([CH:21]=[CH2:22])=[C:2]([NH2:1])[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH3:16])[C:9]=2[F:17])[N:5]=1)=[O:20])[CH2:25][CH2:26][CH3:27]

참가 물질

5

반응물 3

HCID 10962Butyl iodideHCID 11125Lithium CarbonateHCID 468509124-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-ethenylpyrimidine-6-carboxylic acid

생성물 1

HCID 594320876-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-vinyl-pyrimidine-4-carboxylic acid butyl ester수율 52.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-vinyl-pyrimidine-4-carboxylic acid (0.150 g, 0.46 mmol), iodobutane (0.111 g, 0.60 mmol), and lithium carbonate (0.044 g, 0.6 mmol) were combined in DMF (1.5 mL) and heated at 60° C. overnight. The cooled reaction mixture was concentrated and partitioned between ethyl acetate and water. The organic phase was dried and concentrated. The product was purified by flash chromatography on silica gel (ethyl acetate/hexane gradient) to yield the title compound (0.092 g, 52.3% yield): 1H NMR (CDCl3) δ 7.65 (dd, 1H), 7.19 (dd, 1H), 7.75 (dd, 1H), 5.62-5.67 (m, 2H), 5.35 (br s, 2H), 4.34 (t, 3H), 3.99 (dd, 3H), 1.74 (m, 2H), 1.45 (m, 2H), 0.97 (t, 3H).

후처리

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated
  3. custompartitioned between ethyl acetate and water
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customThe product was purified by flash chromatography on silica gel (ethyl acetate/hexane gradient)

출처 및 근거

ORD 기록
ord-9ce36516649743049d0f86678bfd9242
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268753B2

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