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 1660742Notes

Reaction equation

HRID 1660742 reaction equation
[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

Participants

4

Reactant 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

Product 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]pyrimidineYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
22 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-a737c66ab9274dd5b74a2778bc162545
Source dataset
uspto-grants-2011_10
Patent number
US08030304B2

Reaction notes

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