Trimethyl orthoformate → HCID 178420377, compound

HRID 1890278Notes

Reaction equation

HRID 1890278 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH2:15])[C:12]([NH2:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17](OC)(OC)OC>C1COCC1.C(O)(C(F)(F)F)=O>[CH2:1]([O:8][C:9]1[N:14]=[C:13]2[NH:15][CH:17]=[N:16][C:12]2=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 9005Trimethyl orthoformateHCID 673118046-(Benzyloxy)pyridine-2,3-diamine

Product 1

HCID 178420377HCID 178420377, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(benzyloxy)pyridine-2,3-diamine (19.31 g, 89.71 mmol) in THF (300 mL) was added trimethyl orthoformate 99% (99.16 ml, 897.1 mmol) and TFA (345 μL, 4.49 mmol) at room temperature. After stirring for 24 h the solvent was removed under reduced pressure. The residue was taken up in 2 M HCl and EtOAc. The two layers were separated. The organic layer was washed with 2 M HCl and the combined aqueous layers were then made basic by the careful addition of 2 N NaOH. The precipitate was collected by vacuum filtration to give the title compound as a white solid (16.39 g). LCMS m/z=226.3, [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 5.40 (s, 2H), 6.91 (d, J=9.1 Hz, 1H), 7.32 (m, 1H), 7.38 (m, 2H), 7.48 (m, 2H), 8.09 (d, J=9.1 Hz, 1H), 8.79 (s, 1H).

Workup

  1. customwas removed under reduced pressure
  2. customThe two layers were separated
  3. washThe organic layer was washed with 2 M HCl
  4. additionthe combined aqueous layers were then made basic by the careful addition of 2 N NaOH
  5. filtrationThe precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-cceaeff23cb94c0d8cac46f9e4da8d42
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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