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

HRID 32602

Reaction equation

HRID 32602 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

4

Reactant 3

HCID 24841Hydrogen iodideHCID 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%);

Workup

  1. waitat ambient temperature for 24 hours
  2. extractionThe product was extracted with EtOAc (3×15 mL)
  3. dry with materialThe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-36d650d9bef54b7e970ce0e95d3a1b3e
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Linked notes

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