Dimethylformamide → N-(2-methoxyphenethyl)-2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)acetamide

HRID 44421

Reaction equation

HRID 44421 reaction equation
[N:1]1([C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15]([OH:17])=O)[CH:9]=[N:8][C:7]=2[N:5]([CH3:6])[C:3]1=[O:4])[CH3:2].CN(C(ON1N=N[C:28]2[CH:29]=[CH:30][CH:31]=[N:32][C:27]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:42]([O:45][CH2:46][CH3:47])(=O)C.[CH3:48]N(C=O)C>>[CH3:42][O:45][C:46]1[CH:47]=[CH:48][CH:27]=[CH:28][C:29]=1[CH2:30][CH2:31][NH:32][C:15](=[O:17])[CH2:14][N:10]1[C:11]2[C:12](=[O:13])[N:1]([CH3:2])[C:3](=[O:4])[N:5]([CH3:6])[C:7]=2[N:8]=[CH:9]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 69550AcefyllineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 27916152N-(2-methoxyphenethyl)-2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)acetamideYield 24%

Procedure

Compound 101 (600 mg, 2.5 mmol) was mixed with HATU (1.14 g, 3.0 mmol) in 20 mL of DMF under N2 and stirred at room temperature for 20 min. Compound 116 (0.36 mL, 2.5 mmol) was then added. The resulting mixture was stirred overnight and then ethyl acetate (100 mL) was added. The resulting solution was washed with water (3×80 mL) and brine (80 mL) and dried over Na2SO4. During drying some solid precipitates appeared, methanol (10 mL) was added to dissolve the precipitates and then the solution was filtered. The filtrate was concentrated in vacuo and the solid residue was purified by flash column chromatography on 40 g of silica gel with EtOAc/hexanes as eluent. The purified product was triturated with ether (25 mL) and filtered to yield 403 as a white solid (224 mg, 24%). MS (APCI): m/z 372 [M+H]+. Anal. Calcd for C18H21N5O4: C, 58.21; H, 5.70; N, 18.86. Found: C, 58.26; H, 5.73; N, 18.74.

Workup

  1. stirringThe resulting mixture was stirred overnight
  2. washThe resulting solution was washed with water (3×80 mL) and brine (80 mL)
  3. dry with materialdried over Na2SO4
  4. customDuring drying some solid
  5. customprecipitates
  6. additionmethanol (10 mL) was added
  7. dissolutionto dissolve the
  8. customprecipitates
  9. filtrationthe solution was filtered
  10. concentrationThe filtrate was concentrated in vacuo
  11. customthe solid residue was purified by flash column chromatography on 40 g of silica gel with EtOAc/hexanes as eluent
  12. customThe purified product was triturated with ether (25 mL)
  13. filtrationfiltered

Sources & evidence

ORD record
ord-f6db3c29f22d4ac5a46efbd298d2f968
Source dataset
uspto-grants-2013_09
Patent number
US08541423B2

Linked notes

Loading…