Barbituric Acid → HCID 58457051, compound

HRID 245561Notes

Reaction equation

HRID 245561 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([C:11]3[CH:16]=[N:15][CH:14]=[CH:13][N:12]=3)[C:6]=2[CH:5]=[C:4]([CH:17]=O)[C:3]=1[N:19]1[CH2:24][C@H:23]([CH3:25])[O:22][C@H:21]([CH3:26])[CH2:20]1.[NH:27]1[C:32](=[O:33])[CH2:31][C:30](=[O:34])[NH:29][C:28]1=[O:35]>C(O)(C)C>[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([C:11]3[CH:16]=[N:15][CH:14]=[CH:13][N:12]=3)[C:6]=2[CH:5]=[C:4]2[C:3]=1[N:19]1[CH2:24][C@@H:23]([CH3:25])[O:22][C@@H:21]([CH3:26])[C@@H:20]1[C:31]1([C:30](=[O:34])[NH:29][C:28](=[O:35])[NH:27][C:32]1=[O:33])[CH2:17]2

Participants

4

Reactant 2

HCID 6211Barbituric AcidHCID 87368742HCID 87368742, compound2×

Product 1

HCID 58457051HCID 58457051, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

Isopropanol (10 ml) was added to 7-chloro-6-((2R,6S)-2,6-dimethylmorpholino)-3-(pyrazin-2-yl)benzo[d]isoxazole-5-carbaldehyde (Intermediate 472, 198 mg, 0.53 mmol) to give a yellow slurry. The pyrimidine-2,4,6(1H,3H,5H)-trione (barbituric acid) (68.0 mg, 0.53 mmol) was added and the yellow mixture was heated to 80° C. The resulting solution was stirred overnight. The resulting off-white suspension cooled to room temperature, then filtered. The filtercake was washed with MeOH/hexanes to give a white solid, 171 mg (67%).

Workup

  1. customto give a yellow slurry
  2. temperatureThe resulting off-white suspension cooled to room temperature
  3. filtrationfiltered
  4. washThe filtercake was washed with MeOH/hexanes
  5. customto give a white solid, 171 mg (67%)

Sources & evidence

ORD record
ord-21618650ad4e4a6d8f9fd664714a84f1
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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