Barbituric Acid → (2R,4S,4aS)-rel-11-chloro-2,4,8-trimethyl-1,2,4,4a-tetrahydro-2'H,6H-spiro[1,4-oxazino[4,3-a][1,2]oxazolo[4,5-g]quinoline-5,5'-pyrimidine]-2',4',6'(1'H,3'H)-trione

HRID 578012Notes

Reaction equation

HRID 578012 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([CH3:11])[C:6]=2[CH:5]=[C:4]([CH:12]=O)[C:3]=1[N:14]1[CH2:19][C@H:18]([CH3:20])[O:17][C@H:16]([CH3:21])[CH2:15]1.[NH:22]1[C:29](=[O:30])[CH2:28][C:26](=[O:27])[NH:25][C:23]1=[O:24]>CC(O)C>[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([CH3:11])[C:6]=2[CH:5]=[C:4]2[C:3]=1[N:14]1[CH2:15][C@@H:16]([CH3:21])[O:17][C@@H:18]([CH3:20])[C@@H:19]1[C:28]1([C:26](=[O:27])[NH:25][C:23](=[O:24])[NH:22][C:29]1=[O:30])[CH2:12]2

Participants

4

Reactant 2

HCID 6211Barbituric AcidHCID 873697927-Chloro-6-[(2r,6s)-2,6-dimethylmorpholin-4-yl]-3-methyl-1,2-benzoxazole-5-carbaldehyde2×

Product 1

HCID 67432471(2R,4S,4aS)-rel-11-chloro-2,4,8-trimethyl-1,2,4,4a-tetrahydro-2'H,6H-spiro[1,4-oxazino[4,3-a][1,2]oxazolo[4,5-g]quinoline-5,5'-pyrimidine]-2',4',6'(1'H,3'H)-trione

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 7-chloro-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-3-methyl-1,2-benzoxazole-5-carbaldehyde (Intermediate 375, 35 mg, 0.119 mmol) in IPA was added barbituric acid (16 mg, 0.113 mmol) and the mixture heated at 85° C. for 16 hours. Solvents were evaporated and the residue thus obtained was purified over silica column using a gradient of methanol in chloroform to give product as a solid. Yield: 10 mg (25%).

Workup

  1. customSolvents were evaporated
  2. customthe residue thus obtained
  3. customwas purified over silica column
  4. customto give product as a solid

Sources & evidence

ORD record
ord-abe073e5354146d5a3899ee4d9001a7f
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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