Sodium Hydroxide → 5-(2-Ethoxyphenyl)-1,6-dihydro-1,3-dimethyl-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 862905Notes

Reaction equation

HRID 862905 reaction equation
[CH2:1]([O:3][C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[C:6]([NH:8][C:9]1[C:10]([CH3:18])=[N:11][N:12]([CH3:17])[C:13]=1[C:14]([NH2:16])=[O:15])=O)[CH3:2].[OH-].[Na+]>>[CH2:1]([O:3][C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[C:6]1[NH:16][C:14](=[O:15])[C:13]2[N:12]([CH3:17])[N:11]=[C:10]([CH3:18])[C:9]=2[N:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 21250796HCID 21250796, compound

Product 1

HCID 1354336455-(2-Ethoxyphenyl)-1,6-dihydro-1,3-dimethyl-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions

Temperature
140 °C

Procedure

4-(2-Ethoxybenzamido)-1,3-dimethylpyrazole-5-carboxamide (1.6 g, 5.29 mmol) was added to polyphosphoric acid (50 g) and the mixture heated to 140° C. for 6 hours. The solution was cooled, poured into ice-water (100 ml), and then the mixture was basified with 10% aqueous sodium hydroxide solution and extracted with dichloromethane (3×100 ml). The organic extracts were combined, dried (MgSO4) and evaporated under vacuum. The residue was chromatographed on silica gel eluting with a 97:3 mixture of dichloromethane and methanol. Crystallisation of the crude product from aqueous ethanol gave the title compound as a colourless solid, m.p. 201°-204° C. Found: C,63.43; H, 5,57; N,19.35. C15H16N4O2 requires C,63.36; H, 5.67; N,19.71%.

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with dichloromethane (3×100 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated under vacuum
  5. customThe residue was chromatographed on silica gel eluting with a 97:3 mixture of dichloromethane and methanol
  6. customCrystallisation of the crude product from aqueous ethanol

Sources & evidence

ORD record
ord-2eacf98e9184416aa68edbe033613799
Source dataset
uspto-grants-1998_02
Patent number
US05719283

Reaction notes

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