HCID 86703127, compound → HCID 86703126, compound

HRID 2204320Notes

Reaction equation

HRID 2204320 reaction equation
[N:1]([CH:4]1[CH2:9][N:8]([CH3:10])[C:7](=[O:11])[N:6]([CH3:12])[CH2:5]1)=[N+]=[N-]>CCO.[Pd]>[NH2:1][CH:4]1[CH2:9][N:8]([CH3:10])[C:7](=[O:11])[N:6]([CH3:12])[CH2:5]1

Participants

4

Reactant 1

HCID 86703127HCID 86703127, compound

Product 1

HCID 86703126HCID 86703126, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-azido-1,3-dimethyl-tetrahydro-pyrimidin-2-one (Step P5) (2.5 g, 11.1 mmol) and Pd/C 10% (500 mg) in EtOH (70 mL) was stirred at rt under a hydrogen atmosphere for 13.5 h. The reaction mixture was filtered through a pad of celite, washed with THF and MeOH and concentrated. The residue was dissolved in EtOAc and extracted with cold 1N HCl. The aqueous phase was basified with a saturated aqueous NaHCO3 solution. The resulting aqueous phase was extracted with CH2Cl2/isopropanol 3:1 (3×). The combined organic layers were dried (Na2SO4), filtered and concentrated to afford the title compound. ESI-MS: [M+H]+ 144.1 (MS 1).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washwashed with THF and MeOH
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in EtOAc
  5. extractionextracted with cold 1N HCl
  6. extractionThe resulting aqueous phase was extracted with CH2Cl2/isopropanol 3:1 (3×)
  7. dry with materialThe combined organic layers were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6da39042df724714b7d1c5a0d66477ee
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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