Hydrogen Peroxide → HCID 46936067, compound

HRID 515500Notes

Reaction equation

HRID 515500 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C@H:9]2[CH2:15][N:14]([C:16]3[N:17]([CH3:29])[C:18](=[O:28])[CH:19]=[C:20]([C:22]4[CH:27]=[CH:26][N:25]=[CH:24][N:23]=4)[N:21]=3)[CH2:13][CH2:12][CH2:11][O:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[O:30]1CCCC1.C(=O)([O-])[O-].[Na+].[Na+].OO>C(O)C>[CH3:29][N:17]1[C:18](=[O:28])[CH:19]=[C:20]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][N:23]=2)[N:21]=[C:16]1[N:14]1[CH2:13][CH2:12][CH2:11][O:10][C@@H:9]([C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[C:1]([NH2:2])=[O:30])[CH2:15]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 67281239HCID 67281239, compound

Product 1

HCID 46936067HCID 46936067, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)-2-[2-(3-cyano-phenyl)-[1,4]oxazepan-4-yl]-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (A039) (300 mg, 0.772 mmol), tetrahydrofuran (1.90 ml) and 3.0N-sodium carbonate (1.90 ml) in ethanol (1.90 ml) was added 30%-hydrogen peroxide (1.90 ml) at room temperature. The mixture was stirred at room temperature for 2 hours and partitioned between water and chloroform. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was washed with diethyl ether to afford (S)-3-[4-(1-Methyl-6-oxo-1,6-dihydro-[4,4′]bipyrimidinyl-2-yl)-[1,4]oxazepan-2-yl]-benzamide (A015) as pale yellow solid (293 mg, 93%).

Workup

  1. custompartitioned between water and chloroform
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-bfef0aeb99b54c5a8024f3923a16dd08
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Reaction notes

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