Methanol → HCID 86611053, compound

HRID 502614Notes

Reaction equation

HRID 502614 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].C[O-].[Na+].CO.[CH:11]([C:15]1[C:16]([CH3:34])=[CH:17][C:18]([I:33])=[C:19]([CH:32]=1)[O:20][C:21](=[CH:24]NC1C=CC=CC=1)[C:22]#[N:23])=[CH:12][CH:13]=[CH2:14]>C(O)C>[CH:11]([C:15]1[C:16]([CH3:34])=[CH:17][C:18]([I:33])=[C:19]([CH:32]=1)[O:20][C:21]1[C:22]([NH2:23])=[N:4][C:3]([NH2:5])=[N:2][CH:24]=1)=[CH:12][CH:13]=[CH2:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 5742Guanidine HydrochlorideHCID 10942334Sodium MethoxideHCID 86611051HCID 86611051, compound

Product 1

HCID 86611053HCID 86611053, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of guanidine hydrochloride (3.10 g, 32.5 mmol) in 10 mL ethanol was added a solution of 25% NaOMe in methanol (7.0 mL, 32.5 mmol). The resulting solution was added to the crude 2-(5-buta-1,3-dienyl-2-iodo-4-methyl-phenoxy)-3-phenylamino-acrylonitrile of step 4, and the mixture was heated to reflux under nitrogen for 16 hours. The reaction mixture was cooled, concentrated under reduced pressure, diluted with water, and extracted with methylene chloride. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed on silica (10% MeOH/methylene chloride+0.1% NH4OH), and recrystallized from EtOAc to give 2.1 g of 5-(5-buta-1,3-dienyl-2-iodo-4-methyl-phenoxy)-pyrimidine-2,4-diamine, MP=195-197° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux under nitrogen for 16 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. additiondiluted with water
  6. extractionextracted with methylene chloride
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was chromatographed on silica (10% MeOH/methylene chloride+0.1% NH4OH)
  12. customrecrystallized from EtOAc

Sources & evidence

ORD record
ord-7644b019cc884df183cdbd979cabaa13
Source dataset
uspto-grants-2010_08
Patent number
US07776872B2

Reaction notes

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