Ammonium Chloride → 7-(1-Ethyl-propyl)-3-(2-methoxymethyl-thiazol-5-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

HRID 1660751ノート

反応式

HRID 1660751 の反応式
C([Li])CCC.[CH2:6]([CH:8]([C:11]1[N:16]2[N:17]=[C:18]([CH3:25])[C:19]([C:20]3[S:24][CH:23]=[N:22][CH:21]=3)=[C:15]2[N:14]=[C:13]([CH3:26])[CH:12]=1)[CH2:9][CH3:10])[CH3:7].[CH3:27][O:28][CH2:29]I.[Cl-].[NH4+]>C1COCC1>[CH2:6]([CH:8]([C:11]1[N:16]2[N:17]=[C:18]([CH3:25])[C:19]([C:20]3[S:24][C:23]([CH2:27][O:28][CH3:29])=[N:22][CH:21]=3)=[C:15]2[N:14]=[C:13]([CH3:26])[CH:12]=1)[CH2:9][CH3:10])[CH3:7]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 139376Iodomethyl methyl etherHCID 674299217-(1-Ethyl-propyl)-2,5-dimethyl-3-thiazol-5-yl-pyrazolo[1,5-a]pyrimidineHCID 178418339Butyllithium

生成物 1

HCID 674280047-(1-Ethyl-propyl)-3-(2-methoxymethyl-thiazol-5-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine収率 53.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Under a nitrogen atmosphere, add n-butyl lithium (2.5 M in hexane, 0.4 mL, 1.0 mmol) to a solution of 7-(1-ethyl-propyl)-2,5-dimethyl-3-thiazol-5-yl-pyrazolo[1,5-a]pyrimidine (300 mg, 1.0 mmol) in THF (3 mL) at −78° C. Stir 30 min and add 1-iodomethyl methyl ether (205 mg, 1.2 mmol). Continue stirring for one hour and then slowly warm up to room temperature and stir overnight. Quench the reaction by adding saturated ammonium chloride solution and extract with ethyl acetate. Wash the organic layer with brine, dry over sodium sulfate, filter, and concentrate under vacuum to a residue. Purify the crude material by flash chromatography, eluting with hexanes/ethyl acetate (10/2) to give the title compound as a yellow foam (184 mg). MS (APCI) m/z 345.3 (M+1)+.

後処理

  1. stirringContinue stirring for one hour
  2. stirringstir overnight
  3. customQuench
  4. customthe reaction
  5. extractionextract with ethyl acetate
  6. washWash the organic layer with brine
  7. dry with materialdry over sodium sulfate
  8. filtrationfilter
  9. concentrationconcentrate under vacuum to a residue
  10. customPurify the crude material by flash chromatography
  11. washeluting with hexanes/ethyl acetate (10/2)

出典と根拠

ORDレコード
ord-f6926211565b4335b21e8343b767da51
出典データセット
uspto-grants-2011_10
特許番号
US08030304B2

反応ノート

読み込み中…