Sodium Hydroxide → Tert-butyl 5-(2,4-dichlorophenyl)-7-methyl-2-(3-methyl-1,2,4-oxadiazol-5-yl)imidazo[1,2-a]pyrimidine-6-carboxylate

HRID 1868475ノート

反応式

HRID 1868475 の反応式
[C:1]([C:4]1[N:5]=[C:6]2[N:11]=[C:10]([CH3:12])[C:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:8]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[Cl:27])[N:7]2[CH:28]=1)(=[O:3])[NH2:2].[CH3:29][C:30]([N:32](C)C)=O.CC(N(C)C)=O.NO.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.O1CCOCC1.CC(O)=O>[Cl:27][C:21]1[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=1[C:8]1[N:7]2[CH:28]=[C:4]([C:1]3[O:3][N:32]=[C:30]([CH3:29])[N:2]=3)[N:5]=[C:6]2[N:11]=[C:10]([CH3:12])[C:9]=1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 19097097DMA dimethylacetamideHCID 57982465Tert-butyl 2-carbamoyl-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-6-carboxylate

生成物 1

HCID 57982492Tert-butyl 5-(2,4-dichlorophenyl)-7-methyl-2-(3-methyl-1,2,4-oxadiazol-5-yl)imidazo[1,2-a]pyrimidine-6-carboxylate収率 59%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 1140Toluene溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

To a stirred solution of tert-butyl 2-carbamoyl-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-6-carboxylate (60 mg, 0.14 mmol) in PhCH3 (3 mL) was added DMA-DMA (70 μL, 0.43 mmol). The reaction was heated to 90° C. for 2 h and was concentrated to afford the crude ester as a black oil. This crude product was dissolved in dioxane (2 mL) and AcOH (2 mL) and NH2OH.HCl (15 mg, 0.21 mmol) was added followed by NaOH (2N solution, 0.1 mL, 0.2 mmol). After heating to 90° C. for 2 h, the reaction was concentrated under reduced pressure and diluted with EtOAc. The organic layer was washed with H2O and brine prior to drying over anhydrous MgSO4. Filtration, concentration under reduced pressure and purification by silica gel chromatography afforded tert-butyl 5-(2,4-dichlorophenyl)-7-methyl-2-(3-methyl-1,2,4-oxadiazol-5-yl)imidazo[1,2-a]pyrimidine-6-carboxylate (38 mg, 58%) as a yellow solid.

後処理

  1. concentrationwas concentrated
  2. customto afford the crude ester as a black oil
  3. temperatureAfter heating to 90° C. for 2 h
  4. concentrationthe reaction was concentrated under reduced pressure
  5. additiondiluted with EtOAc
  6. washThe organic layer was washed with H2O and brine
  7. dry with materialto drying over anhydrous MgSO4
  8. filtrationFiltration, concentration
  9. customunder reduced pressure and purification by silica gel chromatography

出典と根拠

ORDレコード
ord-a908db72e12543cb96282f489a72b1e2
出典データセット
uspto-grants-2009_12
特許番号
US07635699B2

反応ノート

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