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Ammonium Chloride → 3-(4-Chloro-2-methoxymethyl-thiazol-5-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

HRID 1660752
ノート
印刷プレビュー

反応式

HRID 1660752 の反応式
C([Li])CCC.[CH2:6]([CH:8]([C:11]1[N:16]2[N:17]=[C:18]([CH3:28])[C:19]([C:20]3[S:24][C:23]([CH2:25][O:26][CH3:27])=[N:22][CH:21]=3)=[C:15]2[N:14]=[C:13]([CH3:29])[CH:12]=1)[CH2:9][CH3:10])[CH3:7].[Cl:30]N1C(=O)CCC1=O.[Cl-].[NH4+]>C1COCC1>[Cl:30][C:21]1[N:22]=[C:23]([CH2:25][O:26][CH3:27])[S:24][C:20]=1[C:19]1[C:18]([CH3:28])=[N:17][N:16]2[C:11]([CH:8]([CH2:9][CH3:10])[CH2:6][CH3:7])=[CH:12][C:13]([CH3:29])=[N:14][C:15]=12
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 31398ChlorosuccinimideHCID 674280047-(1-Ethyl-propyl)-3-(2-methoxymethyl-thiazol-5-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidineHCID 178418339Butyllithium

生成物 1

HCID 674285973-(4-Chloro-2-methoxymethyl-thiazol-5-yl)-7-(1-ethyl-propyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine収率 4.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Add n-butyl lithium (2.5 M in hexanes, 174 mL, 0.43 mmol) to a stirred solution of 7-(1-ethyl-propyl)-3-(2-methoxymethyl-thiazol-5-yl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine (150 mg, 0.43 mmol) in THF (3 mL) at −78° C. Stir for 30 min and add N-chlorosuccinimide (87 mg, 0.653 mmol). Stir 30 min and then warm the reaction slowly to room temperature allowing the reaction to continue overnight. Quench the reaction by adding saturated ammonium chloride solution, extract with ethyl acetate, dry over sodium sulfate, filter, and concentrate to a residue. Purify by flash chromatography, eluting with hexanes/ethyl acetate (10/2) to give the title compound (7 mg). MS (APCI) m/z (35Cl) 379.3 (M+1)+.

後処理

  1. stirringStir 30 min
  2. temperaturewarm
  3. customthe reaction slowly to room temperature
  4. customthe reaction
  5. waitto continue overnight
  6. customQuench
  7. customthe reaction
  8. extractionextract with ethyl acetate
  9. dry with materialdry over sodium sulfate
  10. filtrationfilter
  11. concentrationconcentrate to a residue
  12. customPurify by flash chromatography
  13. washeluting with hexanes/ethyl acetate (10/2)

出典と根拠

ORDレコード
ord-e3450ec115254cdf9a011e7d9dbacd0e
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08030304B2

反応ノート

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