Trimethyl orthoformate → HCID 9880947, compound

HRID 1612378Notes

Reaction equation

HRID 1612378 reaction equation
[CH2:1]([CH:3]([NH:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([O:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[C:8]=1[NH2:24])[CH2:4][CH3:5])[CH3:2].[CH:25](OC)(OC)OC.C1(O)O[C@H](C)[C@@H](O)C[C@H]1O>C1(C)C=CC=CC=1>[CH2:1]([CH:3]([N:6]1[C:7]2[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([O:14][C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[C:8]=2[N:24]=[CH:25]1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 12303783HCID 12303783, compoundHCID 219121512-(2,4,6-trimethylphenoxy)-N4-(1-ethylpropyl)-6-methyl-pyridine-3,4-diamine

Product 1

HCID 9880947HCID 9880947, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N4-(1-ethylpropyl)-6-methyl-2-(2,4,6-trimethylphenoxy)-pyridine-3,4-diamine (160 mg, 0.49 mmol), trimethyl orthoformate (62 mg, 0.59 mmol) and paratosylalcohol (p-TsOH) (10 mg) in 20 ml of toluene was heated at reflux under a Dean-Stark trap apparatus for 24 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give the title compound (160 mg, 97%) as a light brown oil. The oil was purified through silica gel column chromatography using 2% methanol (MeOH) in chloroform as eluent to give a tan solid. Mp 127–131° C. 1H NMR (CDCl3) δ 7.82 (s, 1H), 6.90 (s, 2H, 6.81) (s, 1H), 4.02 (m, 1H), 2.37 (s, 3H), 2.32 (s, 3H), 2.13 (s, 6H), 1.98 (m, 4H), 0.87 (t, 6H) ppm.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a Dean-Stark trap apparatus for 24 hours
  3. customThe mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6b7242c328cd44c088ab031e340dcb27
Source dataset
uspto-grants-2006_01
Patent number
US06992188B1

Reaction notes

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