Trifluoroacetic acid → 2-[(6-Methoxy-pyridin-3-ylmethyl)-amino]-pyrimidine-5-carbaldehyde

HRID 1403253Notes

Reaction equation

HRID 1403253 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][N:3]=1.[CH3:10][O:11][C:12]1[N:17]=[CH:16][C:15]([CH:18]=O)=[CH:14][CH:13]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(#N)C>[CH3:10][O:11][C:12]1[N:17]=[CH:16][C:15]([CH2:18][NH:1][C:2]2[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][N:3]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 7690972-Aminopyrimidine-5-carbaldehydeHCID 33645766-Methoxypyridine-3-carbaldehyde

Product 1

HCID 579631992-[(6-Methoxy-pyridin-3-ylmethyl)-amino]-pyrimidine-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a round bottom flask, 2-amino-pyrimidine-5-carbaldehyde (31, 0.750 g, 6.09 mmol), 6-methoxy-pyridine-3-carbaldehyde (29, 1.67 g, 12.2 mmol), trifluoroacetic acid (2.5 mL, 32.0 mmol), and triethylsilane (5.00 mL, 31.3 mmol) were combined with 10 mL of acetonitrile. The reaction was stirred at room temperature overnight, then concentrated under vacuum and combined with aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel flash column chromatography, eluting with 15-100% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound.

Workup

  1. concentrationconcentrated under vacuum
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe resulting material was purified by silica gel flash column chromatography
  7. washeluting with 15-100% ethyl acetate in hexane
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a419b8f27fcb4fb7a4b0390cc688f53d
Source dataset
uspto-grants-2014_12
Patent number
US08912204B2

Reaction notes

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