Sodium Azide → 5-bromo-2-(1H-pyrazol-1-yl)pyrimidine-4,6-diamine

HRID 2401168Notes

Reaction equation

HRID 2401168 reaction equation
[Br:1][C:2]1[C:3]([NH2:14])=[N:4][C:5]([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)=[N:6][C:7]=1Cl.[N-:15]=[N+]=[N-].[Na+]>O1CCOCC1>[Br:1][C:2]1[C:3]([NH2:14])=[N:4][C:5]([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)=[N:6][C:7]=1[NH2:15]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 866770175-bromo-6-chloro-2-(1H-pyrazol-1-yl)pyrimidin-4-amine2×

Product 1

HCID 534678255-bromo-2-(1H-pyrazol-1-yl)pyrimidine-4,6-diamine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.10 g (0.37 mmol) of 5-bromo-6-chloro-2-(1H-pyrazol-1-yl)pyrimidine-4-amine (Intermediate 5) and 0.05 g (0.77 mmol) of sodium azide in dioxane (10 mL) was stirred at 80° C. for 6 h. The solvent was then evaporated, and the residue dissolved in methanol, Pd on charcoal added (10 mg) and hydrogenated for 30 min. The solvent was again evaporated and the residue crystallizes from ethanol.

Workup

  1. customThe solvent was then evaporated
  2. dissolutionthe residue dissolved in methanol
  3. additionPd on charcoal added (10 mg)
  4. customThe solvent was again evaporated
  5. customthe residue crystallizes from ethanol

Sources & evidence

ORD record
ord-3c2b21ac9b854f46891fa63dd5814f14
Source dataset
uspto-grants-2014_08
Patent number
US08796284B2

Reaction notes

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