N-bromobutanimide → HCID 135738546, compound

HRID 1532064Notes

Reaction equation

HRID 1532064 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[NH:19][C:20](=[O:30])[C:21]2[CH:26]=[N:25][N:24]([CH2:27][CH2:28][CH3:29])[C:22]=2[N:23]=1)[CH3:10]>CN(C=O)C>[Br:1][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:9][CH3:10])=[C:13]([C:18]2[NH:19][C:20](=[O:30])[C:21]3[CH:26]=[N:25][N:24]([CH2:27][CH2:28][CH3:29])[C:22]=3[N:23]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 135738567HCID 135738567, compound

Product 1

HCID 135738546HCID 135738546, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-bromosuccinimide (1.0 g, 0.0056 mol) in DMF (10 ml) was added dropwise to a stirred solution of 6-(2-ethoxyphenyl)-1-n-propyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (Example 1; 0.84 g, 0.0028 mol) in DMF (10 ml) and the resulting red solution stirred for 20 hours. The solvent was removed by evaporation under vacuum and the residue partitioned between saturated aqueous sodium bicarbonate solution (20 ml) and ethyl acetate (20 ml). The organic phase was removed and the aqueous phase extracted with ethyl acetate (3×30 ml). The combined organic solutions were dried and the solvent removed by evaporation under vacuum to give an orange crystalline solid. Recrystallisation from ethyl acetate-hexane gave the title compound as colourless crystals (0.812 g, 78%), m.p. 172-173° C. Found: C,51.13; H,4.41; N,14.84. C16H17BrN4O2 requires C,50.94; H,4.54; N,14.85%.

Workup

  1. customThe solvent was removed by evaporation under vacuum
  2. customthe residue partitioned between saturated aqueous sodium bicarbonate solution (20 ml) and ethyl acetate (20 ml)
  3. customThe organic phase was removed
  4. extractionthe aqueous phase extracted with ethyl acetate (3×30 ml)
  5. customThe combined organic solutions were dried
  6. customthe solvent removed by evaporation under vacuum
  7. customto give an orange crystalline solid
  8. customRecrystallisation from ethyl acetate-hexane

Sources & evidence

ORD record
ord-7c7894b237454472a2c344dafe7b1a76
Source dataset
uspto-grants-2001_03
Patent number
US06200980B1

Reaction notes

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