1,3-Dimethyluracil → HCID 136368657, compound

HRID 1483813Notes

Reaction equation

HRID 1483813 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[N:11][NH:12][C:13]=2[NH2:14])[CH:6]=[CH:7][CH:8]=1.CN1[CH:23]=[CH:22][C:21](=[O:24])N(C)C1=O.[O-]CC.[Na+]>C(O)C>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[N:11][N:12]3[CH:23]=[CH:22][C:21](=[O:24])[NH:14][C:13]=23)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 701221,3-DimethyluracilHCID 202258HCID 202258, compoundHCID 2723922Sodium ethoxide

Product 1

HCID 136368657HCID 136368657, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 4-(3-(trifluoromethyl)phenyl)-1H-pyrazol-5-amine (2.7 g, 11.88 mmol) and 1,3-dimethylpyrimidine-2,4(1H,3H)-dione (1.999 g, 14.26 mmol) in ethanol (35 ml) was added sodium ethoxide (1.132 g, 16.64 mmol). After heating to reflux 16 hours under Agonr, the reaction was cooled to RT and the volatiles removed in vacuo. The mixture was diluted with 30 mL H2O and acidified to pH=4 with AcOH. The resulting solid was collected by vacuum filtration. The solid was taken up in a 4:1 DCM/2-propanol solution, washed with water, dried over Na2SO4, and rotovaced to give pure 3-(3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-5(4H)-one (2.07 g, 7.41 mmol, 62.4% yield).

Workup

  1. temperatureAfter heating
  2. temperatureto reflux 16 hours under Agonr
  3. customthe volatiles removed in vacuo
  4. additionThe mixture was diluted with 30 mL H2O
  5. filtrationThe resulting solid was collected by vacuum filtration
  6. washwashed with water
  7. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-e296a3845f6b406ea38db4dde00c6944
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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