Formaldehyde → HCID 18386609, compound

HRID 2298431Notes

Reaction equation

HRID 2298431 reaction equation
[CH2:1]([CH:3]([NH:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([NH:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[C:8]=1[CH2:24][OH:25])[CH2:4][CH3:5])[CH3:2].C=O.[CH3:28]C1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]([CH:3]([N:6]1[C:7]2[C:8](=[C:9]([NH:14][C:15]3[C:16]([CH3:23])=[CH:17][C:18]([CH3:22])=[CH:19][C:20]=3[CH3:21])[N:10]=[C:11]([CH3:13])[CH:12]=2)[CH2:24][O:25][CH2:28]1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 86758656HCID 86758656, compound

Product 1

HCID 18386609HCID 18386609, compoundYield 193.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of [4-(1-ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenylamino)-pyridin-3-yl]-methanol(280 mg, 0.82 mmol), 37% aqueous formaldehyde(0.35 ml) and p-TsOH (78 mg, 0.41 mmol) in 10 ml of toluene was heated at reflux using a Dean-Stark apparatus for 3 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give 280 mg of a green oil. The oil was purified through silica gel column chromatography using EtOAc as eluent to give the title compound as a brown oil. 1H NMR (CDCl3) δ 6.89 (s,2H), 6.09(s,IH), 4.51(s,2H), 4.19(s,2H), 3.53(m,1H), 2.25(s,6H), 2.15(s,6H), 1.55(m,4H), 0.90(t,6H)ppm.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customfor 3 hours
  4. customThe mixture was quenched with water
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was separated
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b3fea6f4ec27455aaea7f8f2faa67967
Source dataset
uspto-grants-2002_12
Patent number
US06492520B1

Reaction notes

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