Iodine → HCID 57606984, compound

HRID 1893906Notes

Reaction equation

HRID 1893906 reaction equation
[I:1]I.[CH2:3]([NH:10][C:11]1[CH:16]=[C:15]([CH3:17])[N:14]=[C:13]([NH2:18])[N:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([NH:10][C:11]1[C:16]([I:1])=[C:15]([CH3:17])[N:14]=[C:13]([NH2:18])[N:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 807Iodine2×HCID 5243908HCID 5243908, compound

Product 1

HCID 57606984HCID 57606984, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Iodine (3.04 g, 12.0 mmol) was added to a solution of N4-benzyl-6-methylpyrimidine-2,4-diamine (2.33 g, 10.9 mmol) in anhydrous MeOH (50 mL) at 0° C. The reaction was allowed to warm to room temperature overnight. After 12 hours, an additional 0.5 equiv of iodine was added, and the reaction warmed to 50° C. After four hours, the reaction was cooled to room temperature and concentrated in vacuo. The residue was diluted with ethyl acetate (200 mL) and washed with 10% NaHSO3 (200 mL). The aqueous phase was separated and washed once more with ethyl acetate (200 mL). The organic phases were combined, washed with brine, separated and dried over Na2SO4, The filtrate was concentrated in vacuo to afford the product N4-benzyl-5-iodo-6-methylpyrimidine-2,4-diamine (3.14 g, 85% yield).

Workup

  1. temperaturethe reaction warmed to 50° C
  2. waitAfter four hours
  3. temperaturethe reaction was cooled to room temperature
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with ethyl acetate (200 mL)
  6. washwashed with 10% NaHSO3 (200 mL)
  7. customThe aqueous phase was separated
  8. washwashed once more with ethyl acetate (200 mL)
  9. washwashed with brine
  10. customseparated
  11. dry with materialdried over Na2SO4
  12. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-50fa307761c34ab28229a0bad44572ed
Source dataset
uspto-grants-2013_08
Patent number
US08513266B2

Reaction notes

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