Tert-butyl {2-fluoro-5-[methyl(5-nitro-4-thiocyanatopyrimidin-2-yl)amino]phenyl}carbamate → Tert-butyl {5-[(2-amino[1,3]thiazolo[5,4-d]pyrimidin-5-yl)(methyl)amino]-2-fluorophenyl}carbamate

HRID 1800696ノート

反応式

HRID 1800696 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:21])[C:9]2[N:14]=[C:13]([S:15][C:16]#[N:17])[C:12]([N+:18]([O-])=O)=[CH:11][N:10]=2)=[CH:4][C:3]=1[NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]>C(O)(=O)C>[NH2:17][C:16]1[S:15][C:13]2[N:14]=[C:9]([N:8]([CH3:21])[C:5]3[CH:6]=[CH:7][C:2]([F:1])=[C:3]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:4]=3)[N:10]=[CH:11][C:12]=2[N:18]=1

参加物

3

反応物 1

HCID 86646077Tert-butyl {2-fluoro-5-[methyl(5-nitro-4-thiocyanatopyrimidin-2-yl)amino]phenyl}carbamate

生成物 1

HCID 86646078Tert-butyl {5-[(2-amino[1,3]thiazolo[5,4-d]pyrimidin-5-yl)(methyl)amino]-2-fluorophenyl}carbamate収率 46%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
80 °C

実験手順

To a solution of the above-mentioned crude product of tert-butyl {2-fluoro-5-[methyl(5-nitro-4-thiocyanatopyrimidin-2-yl)amino]phenyl}carbamate in acetic acid (70 mL) was added reduced iron (4.28 g, 76.7 mmol), and the mixture was stirred at 80° C. for 3 hr. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. To the obtained residue was added 0.5N aqueous sodium hydroxide solution (100 mL), and the mixture was extracted with ethyl acetate (200 mL, 30 mL). The combined organic layer was washed with saturated brine (30 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was washed with tetrahydrofuran to give the title compound (1.95 g, 46%) as a pale-purple solid.

後処理

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the obtained residue was added 0.5N aqueous sodium hydroxide solution (100 mL)
  4. extractionthe mixture was extracted with ethyl acetate (200 mL, 30 mL)
  5. washThe combined organic layer was washed with saturated brine (30 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. washThe obtained residue was washed with tetrahydrofuran

出典と根拠

ORDレコード
ord-7800fe0044804c50b045192ddc227e3e
出典データセット
uspto-grants-2013_01
特許番号
US08344135B2

反応ノート

読み込み中…