Sodium Azide → HCID 86703127, compound

HRID 2204321Notes

Reaction equation

HRID 2204321 reaction equation
[CH3:1][N:2]1[CH2:7][CH:6](OS(C)(=O)=O)[CH2:5][N:4]([CH3:13])[C:3]1=[O:14].[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C=O)C.C(Cl)Cl.C(O)(C)C>[N:15]([CH:6]1[CH2:7][N:2]([CH3:1])[C:3](=[O:14])[N:4]([CH3:13])[CH2:5]1)=[N+:16]=[N-:17]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86703128HCID 86703128, compound

Product 1

HCID 86703127HCID 86703127, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21966342Isopropanol methylene chlorideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methanesulfonic acid 1,3-dimethyl-2-oxo-hexahydro-pyrimidin-5-yl ester (Step P6) (3.2 g, 14.3 mmol) in DMF (75 mL) at rt was added sodium azide (1.9 g, 28.7 mmol) and the mixture was stirred at 70° C. for 13 h. The mixture was diluted with CH2Cl2/isopropanol 3:1 and extracted with a saturated aqueous NaHCO3 solution. The organic phase was dried (Na2SO4), filtered and concentrated to afford the title compound. ESI-MS: [M+H]+ 170.1 (MS 1).

Workup

  1. extractionextracted with a saturated aqueous NaHCO3 solution
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8353b12877ca448e87b9c8b2b3afb77f
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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