Barbituric Acid → HCID 58457057, compound

HRID 245556Notes

Reaction equation

HRID 245556 reaction equation
[CH3:1][C@@H:2]1[CH2:7][N:6]([C:8]2[C:21]([CH:22]=O)=[CH:20][C:11]3[C:12]([C:15]4[S:16][CH:17]=[CH:18][N:19]=4)=[N:13][O:14][C:10]=3[C:9]=2[F:24])[CH2:5][C@@H:4]([CH3:25])[O:3]1.[NH:26]1[C:31](=[O:32])[CH2:30][C:29](=[O:33])[NH:28][C:27]1=[O:34]>C(O)C>[F:24][C:9]1[C:10]2[O:14][N:13]=[C:12]([C:15]3[S:16][CH:17]=[CH:18][N:19]=3)[C:11]=2[CH:20]=[C:21]2[C:8]=1[N:6]1[CH2:7][C@@H:2]([CH3:1])[O:3][C@@H:4]([CH3:25])[C@@H:5]1[C:30]1([C:29](=[O:33])[NH:28][C:27](=[O:34])[NH:26][C:31]1=[O:32])[CH2:22]2

Participants

4

Reactant 2

HCID 6211Barbituric AcidHCID 86658137HCID 86658137, compound2×

Product 1

HCID 58457057HCID 58457057, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-((2R,6R)-2,6-dimethylmorpholino)-7-fluoro-3-(thiazol-2-yl)benzo[d]isoxazole-5-carbaldehyde (Intermediate 430, 1.414 g, 3.91 mmol) and pyrimidine-2,4,6(1H,3H,5H)-trione (0.501 g, 3.91 mmol) in ethanol (200 ml) was heated at 90° C. for 5 days. Solvent removed. LCMS of crude reaction indicates 9:1 mixture of two diastereomeric products. The major product was purified by reverse phase preparative HPLC to give the title compound (1.320 g, 71.6%).

Workup

  1. customSolvent removed
  2. customLCMS of crude reaction
  3. addition9:1 mixture of two diastereomeric products
  4. customThe major product was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-702a97749cf04e33ac9f439969ea2227
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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