N-bromobutanimide → 8-bromo-N-cyclopentyl-2-(methylsulfanyl)-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amine

HRID 1296718Notes

Reaction equation

HRID 1296718 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:15]=[C:11]3[N:10]=[C:9]([S:22][CH3:23])[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:24]N1C(=O)CCC1=O>ClCCl>[Br:24][C:15]1[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:13][N:12]2[C:7]([NH:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[N:8][C:9]([S:22][CH3:23])=[N:10][C:11]=12

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 69449600N-Cyclopentyl-2-(methylsulfanyl)-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amine

Product 1

HCID 694470128-bromo-N-cyclopentyl-2-(methylsulfanyl)-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amineYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Cyclopentyl-2-(methylsulfanyl)-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amine (0.49 g, 1.5 mmol) was dissolved in dichloromethane. To this solution was added N-bromosuccinimide (330 mg, 1.85 mmol) and the resulting solution was stirred at room temperature for 30 minutes. Additional dichloromethane was added and the reaction mixture was extracted with 1N aqueous sodium hydroxide and with water. The organic phase was dried (magnesium sulfate), filtered and concentrated to give a solid. This solid was purified by silica gel chromatography (ethyl acetate:hexane 1:2) to give 0.5 g (82%) of 8-bromo-N-cyclopentyl-2-(methylsulfanyl)-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4-amine as a solid. 1H-NMR (CDCl3): δ 8.05 (m,2H), 7.55 (m,3H), 6.52 (d, 1H), 4.60 (m,1H), 2.66 (s, 3H), 2.3–2.1 (m, 2H), 2.0–1.6 (m, 6H); MS m/z 405 (M+1).

Workup

  1. extractionthe reaction mixture was extracted with 1N aqueous sodium hydroxide and with water
  2. dry with materialThe organic phase was dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a solid
  6. customThis solid was purified by silica gel chromatography (ethyl acetate:hexane 1:2)

Sources & evidence

ORD record
ord-25a3ed71e9594f0ab0d9eebe8f43f792
Source dataset
uspto-grants-2007_07
Patent number
US07247626B2

Reaction notes

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