Sodium Iodide → HCID 90409742, compound

HRID 516577Notes

Reaction equation

HRID 516577 reaction equation
[B-](F)(F)(F)F.N#[O+].[NH2:8][C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18](N)=[CH:17][CH:16]=2)[N:12]=[C:11]([C:22]([O:24][CH3:25])=[O:23])[C:10]=1[CH:26]=[CH2:27].[I-:28].[Na+].[O-]S([O-])=O.[Na+].[Na+]>ClCCl.O1CCOCC1.O>[NH2:8][C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([I:28])=[CH:17][CH:16]=2)[N:12]=[C:11]([C:22]([O:24][CH3:25])=[O:23])[C:10]=1[CH:26]=[CH2:27]

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 24437Sodium SulfiteHCID 11137142Nitrilooxonium tetrafluoroborateHCID 90408789HCID 90408789, compound

Product 1

HCID 90409742HCID 90409742, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a 50-mL round bottom flask, equipped with a stir bar, was added nitrosyl tetrafluoroborate (78 mg, 0.67 mmol) and dichloromethane (2.0 mL). The flask was cooled in a ice water bath and placed under N2 atmosphere. Then methyl 6-amino-2-(4-aminophenyl)-5-vinylpyrimidine-4-carboxylate (180 mg, 0.666 mmol) in dichloromethane (2.5 mL) was added dropwise. The reaction was allowed to stir for 60 min. Then sodium iodide (499 mg, 3.33 mmol) in a minimal amount of H2O was added, followed by dioxane (1.0 mL). The reaction was allowed to stir for 18 hrs at room temperature. The reaction mixture was poured into saturated Na2SO3 solution and extracted with ethyl acetate (3×50 L). The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated. The resulting residue was purified by flash chromatography (Silica gel, 0-30% EtOAc in Hexanes), and reverse phase chromatography to afford the title compound as a light yellow solid (0.068 g, 27%).

Workup

  1. customTo a 50-mL round bottom flask, equipped with a stir bar
  2. temperatureThe flask was cooled in a ice water bath
  3. stirringto stir for 18 hrs at room temperature
  4. extractionextracted with ethyl acetate (3×50 L)
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by flash chromatography (Silica gel, 0-30% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-843ecebfb1dd4af4991f6efb6a2468b5
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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