N-bromobutanimide → 5-(5-Bromo-2-propoxyphenyl)-1,6-dihydro-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 21926Notes

Reaction equation

HRID 21926 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[NH:20][C:21](=[O:32])[C:22]2[N:27]([CH3:28])[N:26]=[C:25]([CH2:29][CH2:30][CH3:31])[C:23]=2[N:24]=1)[CH2:10][CH3:11]>CN(C)C=O>[Br:1][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:9][CH2:10][CH3:11])=[C:14]([C:19]2[NH:20][C:21](=[O:32])[C:22]3[N:27]([CH3:28])[N:26]=[C:25]([CH2:29][CH2:30][CH3:31])[C:23]=3[N:24]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1357385471-Methyl-5-(2-propoxyphenyl)-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

Product 1

HCID 1361515895-(5-Bromo-2-propoxyphenyl)-1,6-dihydro-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-oneYield 83.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N-Bromosuccinimide (2,6g, 0.016 mol) in dimethylformamide (40 ml) was added dropwise to a stirred solution of 5-(2-n-propoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (Preparation 10, 4.0 g, 0.010 mol) in dimethylformamide (40 ml) at room temperature. After 7 hours the solvent was removed by evaporation under vacuum, the residue suspended in saturated aqueous sodium carbonate solution, and the resulting solution extracted with ethyl acetate (3×50 ml). The organic extracts were combined, dried (Na2SO4) and evaporated under vacuum. Trituration of the residue with ether, followed by crystallisation from ethyl acetate-hexane, gave the title compound as white crystals (3.39 g, 68%), m.p. 117°-118° C. Found: C,53.15; H,5.03; N,13,78. C18H21BrN4O2 requires C,53,34; N,5.22; N,13.82%.

Workup

  1. customAfter 7 hours the solvent was removed by evaporation under vacuum
  2. extractionthe resulting solution extracted with ethyl acetate (3×50 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated under vacuum
  5. customTrituration of the residue with ether, followed by crystallisation from ethyl acetate-hexane

Sources & evidence

ORD record
ord-fc8cc235d64146bfadb6bab711d291de
Source dataset
uspto-grants-1995_06
Patent number
US05426107

Reaction notes

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