Stannous chloride dihydrate → HCID 10967548, compound

HRID 377500Notes

Reaction equation

HRID 377500 reaction equation
[N:1]1([C:6]2[N:11]=[C:10]([N:12]3[CH:16]=[CH:15][N:14]=[CH:13]3)[C:9]([N+:17]([O-])=O)=[C:8]([CH:20]([CH3:22])[CH3:21])[N:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.O.O.[Sn](Cl)Cl>C(O)C>[N:1]1([C:6]2[N:11]=[C:10]([N:12]3[CH:16]=[CH:15][N:14]=[CH:13]3)[C:9]([NH2:17])=[C:8]([CH:20]([CH3:22])[CH3:21])[N:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 53792902HCID 53792902, compound

Product 1

HCID 10967548HCID 10967548, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 2,4-bis(1H-imidazol-1-yl)-5-nitro-6-(2-propyl)pyrimidine (16 g, 53.5 mmol) in 300 mL of ethanol and add 35 g of tin (II) chloride dihydrate. Stir for 2 hours at ambient temperature. Remove the solvent under vacuum and slurry the residue in 2 L of CH2Cl2. Wash with 2×3 L 10% KOH. Dry the CH2Cl2 portion over MgSO4, treat with charcoal, filter, and concentrate the filtrate under vacuum. Crystallize the residue from ethyl acetate to provide 2,4-bis(1H-imidazol-1-yl)-6-(2-propyl)pyrimidin-5-amine.

Workup

  1. customRemove the solvent under vacuum
  2. washWash with 2×3 L 10% KOH
  3. dry with materialDry the CH2Cl2 portion over MgSO4
  4. additiontreat with charcoal
  5. filtrationfilter
  6. concentrationconcentrate the filtrate under vacuum
  7. customCrystallize the residue from ethyl acetate

Sources & evidence

ORD record
ord-c14fb4bc005b4880828a8b1c25e04c88
Source dataset
uspto-grants-2000_02
Patent number
US06025489

Reaction notes

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