Methyl iodide → 2-Methyl-6-(methyloxy)-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amine

HRID 573562ノート

反応式

HRID 573562 の反応式
[NH2:1][C:2]1[C:3]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)=[C:10]([CH3:20])[S:9][C:4]=2[NH:5][C:6](=[O:8])[CH:7]=1.[C:21](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH3:20][C:10]1[S:9][C:4]2[N:5]=[C:6]([O:8][CH3:21])[CH:7]=[C:2]([NH2:1])[C:3]=2[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 683240244-Amino-2-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-6(7H)-one

生成物 1

HCID 683241312-Methyl-6-(methyloxy)-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amine収率 13.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a suspension of 4-amino-2-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-6(7H)-one (Description 36) (120 mg, 0.419 mmol) in DMF (3 mL) was added potassium carbonate (116 mg, 0.838 mmol) and methyl iodide (0.029 mL, 0.461 mmol). The suspension was then heated to 90° C. under nitrogen atmosphere for ca. 2 hand then cooled to RT, quenched with water (ca. 25 mL) and extracted with ethyl acetate (ca. 25 mL×2). The combined organic layers were passed through a phase separator and solvent concentrated in vacuo. The residue was purified by normal phase chromatography, eluting with a gradient of 0-100% ethyl acetate in DCM followed by 0-20% MeOH in DCM, to afford the title compound (16.5 mg). LCMS (A) m/z: 301 [M+1]+, Rt 1.21 min (acidic).

後処理

  1. temperaturethen cooled to RT
  2. customquenched with water (ca. 25 mL)
  3. extractionextracted with ethyl acetate (ca. 25 mL×2)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by normal phase chromatography
  6. washeluting with a gradient of 0-100% ethyl acetate in DCM

出典と根拠

ORDレコード
ord-ac98575473d0415792aef8c2702d2b2e
出典データセット
uspto-grants-2015_05
特許番号
US09029545B2

反応ノート

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