Acetic Acid → HCID 178448865, compound

HRID 885637Notes

Reaction equation

HRID 885637 reaction equation
[CH:1]([NH:4][C:5]1[N:10]=[C:9]([C:11](=O)[C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=O)[CH:8]=[CH:7][N:6]=1)([CH3:3])[CH3:2].[CH2:22]1[N:27]2CN3CN(C2)C[N:23]1C3.[O-]S([O-])(=O)=O.[Na+].[Na+].[CH3:39]C(O)=O>>[C:1]([NH:4][C:5]1[N:10]=[C:9]([C:11]2[N:23]=[CH:22][NH:27][C:12]=2[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH:8]=[CH:7][N:6]=1)([CH3:39])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 24436Sodium SulfateHCID 121652381-(2-iso-propylamino-pyrimidin-4-yl)-2-(4-fluoro-phenyl)-ethane-1,2-dione

Product 1

HCID 178448865HCID 178448865, compoundYield 52%

Conditions

Temperature
65 °C

Procedure

A mixture of 1-(2-iso-propylamino-pyrimidin-4-yl)-2-(4-fluoro-phenyl)-ethane-1,2-dione (12.5 g, 43.5 mmol), hexamethylenetetramine (12.2 g, 87.1 mmol), NH4OAc (17 g, 220 mmol), and Na2SO4 (12 g) in AcOH (150 mL) was heated at 65° C. After 4 h, the mixture was cooled to rt. The mixture was filtered, washing with AcOH. The filtrate was concentrated, and the residue was dissolved in CH2Cl2. The organic solution was washed with 1 N NaOH, dried (Na2SO4), and concentrated. The crude product was purified by column chromatography (MeOH/hexanes) to afford the title compound as a light yellow solid (6.8 g, 52%). TLC (10% MeOH/CH2Cl2): Rf=0.21. 1H NMR: 8.13 (br s, 1H), 7.84 (br s, 1H), 7.61 (br s, 2H), 7.14 (t, J=7.8 Hz, 2H), 6.87 (br s, 1H), 5.31 (br s, 1H), 4.14 (br s, 1H), 1.26 (d, J=9.8 Hz, 6H). HRMS (ESI): [M+H]+ calcd. for C16H17FN5, 298.1463; found, 298.1461.

Workup

  1. temperaturethe mixture was cooled to rt
  2. filtrationThe mixture was filtered
  3. washwashing with AcOH
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe residue was dissolved in CH2Cl2
  6. washThe organic solution was washed with 1 N NaOH
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (MeOH/hexanes)

Sources & evidence

ORD record
ord-89edf7c0f9b8488881691853afd6b8bd
Source dataset
uspto-grants-2012_08
Patent number
US08242273B2

Reaction notes

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