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

HRID 44422

Reaction equation

HRID 44422 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[C:27]1=2)=[N+](C)C)C.[F:35][P-](F)(F)(F)(F)F.CCO[C:45]([CH3:47])=O.C[N:49]([CH:51]=O)C>>[F:35][C:45]1[CH:47]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:27][CH2:51][NH:49][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 28010248N-(2-fluorophenethyl)-2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-yl)acetamideYield 31%

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 117 (0.33 mL, 2.5 mmol) was added. The resulting mixture was stirred overnight. EtOAc (100 mL) was added and the resulting solution was washed with water (3×80 mL) and brine (80 mL), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the resulting solid residue was purified by flash column chromatography on 40 g of silica gel eluting with EtOAc/hexanes. The purified product was triturated with ether (30 mL) and filtered to yield 404 as a white solid (281 mg, 31%). MS (APCI): m/z 360 [M+H]+. Anal. Calcd for C17H18FN5O3.0.3H2O: C, 55.98; H, 5.14; N, 19.20. Found: C, 55.87; H, 5.07; N, 19.13.

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. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe resulting solid residue was purified by flash column chromatography on 40 g of silica gel eluting with EtOAc/hexanes
  7. customThe purified product was triturated with ether (30 mL)
  8. filtrationfiltered

Sources & evidence

ORD record
ord-9df56a9e7f7f404d886ced3a34f416b6
Source dataset
uspto-grants-2013_09
Patent number
US08541423B2

Linked notes

Loading…