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N-bromobutanimide → 3-[4-Bromo-2-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiazol-5-yl]-2,5-dimethyl-7-(1-propyl-butyl)-pyrazolo[1,5-a]pyrimidine

HRID 1660742
ノート
印刷プレビュー

反応式

HRID 1660742 の反応式
[CH3:1][C:2]1[C:18]([C:19]2[S:23][C:22]([C:24]3[N:25]([CH3:29])[N:26]=[CH:27][N:28]=3)=[N:21][CH:20]=2)=[C:5]2[N:6]=[C:7]([CH3:17])[CH:8]=[C:9]([CH:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])[N:4]2[N:3]=1.[Br:30]N1C(=O)CCC1=O>C(#N)C>[Br:30][C:20]1[N:21]=[C:22]([C:24]2[N:25]([CH3:29])[N:26]=[CH:27][N:28]=2)[S:23][C:19]=1[C:18]1[C:2]([CH3:1])=[N:3][N:4]2[C:9]([CH:10]([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])=[CH:8][C:7]([CH3:17])=[N:6][C:5]=12
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 674286482,5-Dimethyl-3-[2-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiazol-5-yl]-7-(1-propyl-butyl)-pyrazolo[1,5-a]pyrimidine

生成物 1

HCID 247588853-[4-Bromo-2-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiazol-5-yl]-2,5-dimethyl-7-(1-propyl-butyl)-pyrazolo[1,5-a]pyrimidine収率 77%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
22 °C

実験手順

To a solution of 2,5-dimethyl-3-[2-(2-methyl-2H-[1,2,4]triazol-3-yl)-thiazol-5-yl]-7-(1-propyl-butyl)-pyrazolo[1,5-a]pyrimidine (6 g, 14.65 mmol) in acetonitrile (60 mL) add N-bromosuccinimide (2.74 g, 15.4 mmol) in one portion and stir at 22° C. for 10 h. Evaporate the solvent and dissolve the residue in a mixture of water (50 mL) and methyl-t-butyl ether (100 mL). Separate the organic layer and extract the aqueous layer with additional methyl-t-butyl ether (2×50 mL). Combine the organic portions and evaporate the solvent. Purify the resulting material by filtration through a silica gel pad, eluting with hexanes/ethyl acetate (3/1). Combine the product containing fractions and evaporate the solvent. Add heptanes (25 mL) and triturate the solid. Filter the solid and dry under vacuum to afford the title compound (5.5 g, 77%). ES/MS m/z (79Br/81Br) 488/490 (M+1)+.

後処理

  1. customEvaporate the solvent
  2. dissolutiondissolve the residue
  3. additionin a mixture of water (50 mL) and methyl-t-butyl ether (100 mL)
  4. customSeparate the organic layer
  5. extractionextract the aqueous layer with additional methyl-t-butyl ether (2×50 mL)
  6. customCombine the organic portions and evaporate the solvent
  7. customPurify the resulting material
  8. filtrationby filtration through a silica gel pad
  9. washeluting with hexanes/ethyl acetate (3/1)
  10. additionCombine the product containing fractions
  11. customevaporate the solvent
  12. customAdd heptanes (25 mL) and triturate the solid
  13. filtrationFilter the solid
  14. customdry under vacuum

出典と根拠

ORDレコード
ord-a737c66ab9274dd5b74a2778bc162545
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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