Triethylamine → HCID 54730629, compound

HRID 547378Notes

Reaction equation

HRID 547378 reaction equation
C([O:7][C:8]1[C:13](=[O:14])[N:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]2=[N:10][C:9]=1[C:19]([O:21]C)=O)(=O)C(C)(C)C.[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1.C(N(CC)CC)C>CO>[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:29][C:19]([C:9]2[N:10]=[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][N:12]3[C:13](=[O:14])[C:8]=2[OH:7])=[O:21])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 67198751HCID 67198751, compound

Product 1

HCID 54730629HCID 54730629, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
60 °C

Procedure

Methyl 3-[(pivaloyl)oxy]-4-oxo-4H-pyrido[1,2-a]pyrimidine-2-carboxylate was dissolved in methanol. p-Fluorobenzylamine (2 eqs.) was added and the reaction was stirred and heated to 60° C. for 2 hours. A precipitate had formed and further methanol and 1 eq. of triethylamine were added. After 2 more hours at 60° C. the reaction mixture was partitioned between EtOAc and 1 M HCl. The organic phase was extracted with 0.1 M aqueous NaOH. The aqueous phase was separated and acidified with 1 M HCl. The aqueous phase was extracted with EtOAc and the organic phase was dried over Na2SO4, filtered and concentrated to dryness. The title compound was obtained as a yellow solid.

Workup

  1. customA precipitate had formed
  2. customAfter 2 more hours at 60° C. the reaction mixture was partitioned between EtOAc and 1 M HCl
  3. extractionThe organic phase was extracted with 0.1 M aqueous NaOH
  4. customThe aqueous phase was separated
  5. extractionThe aqueous phase was extracted with EtOAc
  6. dry with materialthe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-1f3036b512404e53830b69701d430c8f
Source dataset
uspto-grants-2011_05
Patent number
US07939537B2

Reaction notes

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