1,3-Dimethyluracil → Pyrazolo[1,5-a]pyriMidin-5(4H)-one

HRID 2098021Notes

Reaction equation

HRID 2098021 reaction equation
C[N:2]1[CH:9]=[CH:8][C:6](=[O:7])[N:5](C)[C:3]1=O.[O-]CC.[Na+].[NH:15]1[C:19](N)=[CH:18]C=N1>C(O)C>[N:15]1[N:2]2[CH:9]=[CH:8][C:6](=[O:7])[NH:5][C:3]2=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 701221,3-DimethyluracilHCID 74561Pyrazol-3-ylamineHCID 2723922Sodium ethoxide

Product 1

HCID 135513288Pyrazolo[1,5-a]pyriMidin-5(4H)-oneYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

1,3-Dimethyl uracil (3.15 g, 22.5 mmol) and sodium ethoxide (23 mL of a 21% solution in ethanol) were added to a solution of 1H-pyrazol-5-amine (1.7 g, 20.4 mmol) in ethanol (50 mL). The resulting mixture was heated to 60° C. for 2 h and was then cooled to room temperature. The pale brown solid was isolated by filtration to give pyrazolo[1,5-a]pyrimidin-5(4H)-one (1.6 g, 58%). Retention time (min)=0.820, method [3], MS (ESI) 136.1 (M+H).

Workup

  1. temperaturewas then cooled to room temperature
  2. customThe pale brown solid was isolated by filtration

Sources & evidence

ORD record
ord-71e856259acd400dbfa3d0b493fdbe07
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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