Hydrogen iodide → 6-Iodopyrimidine-4,5-diamine

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[NH2:9].[IH:10].C([O-])(O)=O.[Na+]>>[I:10][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[NH2:9]

Participants

Reactant 3

HCID 24841Hydrogen iodide

HCID 780104,5-Pyrimidinediamine, 6-chloro-2×

HCID 516892Sodium Bicarbonate

Product 1

HCID 179658946-Iodopyrimidine-4,5-diamineYield 98%

Conditions

Temperature: 0 °C

Procedure

6-Chloropyrimidine-4,5-diamine (Intermediate 88) (90 mg) was added slowly to HI (57%, aq) (2 mL) at 0° C. The reaction mixture was allowed to stir at 0° C. for 30 minutes and then at ambient temperature for 24 hours. NaHCO3 (sat aq.) was added dropwise until the reaction mixture was pH 8. The product was extracted with EtOAc (3×15 mL). The combined organics were dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a grey solid (144 mg, 98%);