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

HRID 1660751노트

반응식

HRID 1660751 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-f6926211565b4335b21e8343b767da51
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030304B2

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