Imidazole → 5-[2-Ethoxy-5-(1-imidazolyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one

HRID 327051Notes

Reaction equation

HRID 327051 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:22][CH2:23][CH3:24])=[C:6]([C:8]2[NH:9][C:10](=[O:21])[C:11]3[N:16]([CH3:17])[N:15]=[C:14]([CH2:18][CH2:19][CH3:20])[C:12]=3[N:13]=2)[CH:7]=1.[NH:25]1[CH:29]=[CH:28][N:27]=[CH:26]1.C(=O)([O-])[O-].[K+].[K+].II>CN(C)C=O.[Cu].O>[CH2:23]([O:22][C:5]1[CH:4]=[CH:3][C:2]([N:25]2[CH:29]=[CH:28][N:27]=[CH:26]2)=[CH:7][C:6]=1[C:8]1[NH:9][C:10](=[O:21])[C:11]2[N:16]([CH3:17])[N:15]=[C:14]([CH2:18][CH2:19][CH3:20])[C:12]=2[N:13]=1)[CH3:24]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11430Potassium CarbonateHCID 1357385545-(5-Bromo-2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-D]pyrimidin-7(6H)-one

Product 1

HCID 1357385725-[2-Ethoxy-5-(1-imidazolyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(5-bromo-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one (0.20 g, 0.00051 mol), imidazole (0.172 g, 0.0025 mol), anhydrous potassium carbonate (0.077 g, 0.00056 mol), copper bronze (0.036 g, 0.00057 mol) and iodine (0.015 g, 0.00012 mol) in dimethylformamide (10 ml) was heated under reflux under nitrogen for 4.5 hours, cooled and poured into water (50 ml). This mixture was extracted with a 9:1 mixture of dichloromethane and methanol (6×50 ml) and the extracts combined, dried (MgSO4) and evaporated under vacuum to give a pale brown oil. The oil was chromatographed on silica gel (20 g), eluting with a mixture of dichloromethane, methanol and triethylamine (97.8:2:0.2), to give a yellow solid, crystallisation of which from ethyl acetatehexane gave the title compound as a cream solid (0.073 g, 38%, m.p. 193°-194° C. Found: C,63.61; H,5.97; N,22.03. C20H22N6O2 requires C,63.48; H,5.86; N,22.21%.

Workup

  1. temperatureunder reflux under nitrogen for 4.5 hours
  2. temperaturecooled
  3. extractionThis mixture was extracted with a 9:1 mixture of dichloromethane and methanol (6×50 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated under vacuum
  6. customto give a pale brown oil
  7. customThe oil was chromatographed on silica gel (20 g)
  8. washeluting with a mixture of dichloromethane, methanol and triethylamine (97.8:2:0.2)
  9. customto give
  10. customa yellow solid, crystallisation of which from ethyl acetatehexane

Sources & evidence

ORD record
ord-1582a72c0124435aacaaaf761737c1dc
Source dataset
uspto-grants-1993_12
Patent number
US05272147

Reaction notes

Loading…