Sodium Bicarbonate → HCID 178455829, compound

HRID 2093683

Reaction equation

HRID 2093683 reaction equation
[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([C:16]4[CH:21]=[CH:20][N:19]=[C:18](F)[CH:17]=4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:23])[C:8](=[O:24])[C@H:7]2[CH2:25][CH3:26])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])(O)=[O:28].[Na+]>C(O)=O>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([OH:28])[CH:17]=4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:23])[C:8](=[O:24])[C@H:7]2[CH2:25][CH3:26])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 58405345(R)-8-cyclopentyl-7-ethyl-2-(2-fluoropyridin-4-yl)-5-methyl-7,8-dihydropteridin-6(5H)-one

Product 1

HCID 178455829HCID 178455829, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

(R)-8-cyclopentyl-7-ethyl-2-(2-fluoropyridin-4-yl)-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 16, 100 mg, 0.28 mmol) was dissolved in 3 mL of HCOOH. This mixture was heated to reflux for 18 h, then aqueous NaHCO3 was added and the mixture was extracted with EtOAc. The combined organic phase was dried with Na2SO4, concentrated under reduced pressure and chromatographed on flash silica gel (CH2Cl2:CH3OH=6:1) to give the title compound as a white solid (80 mg, 80% yield). 1H NMR (CD3OD) δ: 8.09 (s, 1H), 8.52 (d, 1H) 7.46 (s, 1H), 7.27 (m, 1H), 4.42-4.38 (m, 2H), 3.41 (s, 3H), 2.0-1.7 (m, 10H) and 0.86 ppm (t, 3H); LCMS: 354.2 m/z (M+H)+; ret. Time: 1.36 min (Analytical Method E).

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 18 h
  3. extractionthe mixture was extracted with EtOAc
  4. dry with materialThe combined organic phase was dried with Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed on flash silica gel (CH2Cl2:CH3OH=6:1)

Sources & evidence

ORD record
ord-4d0c535a84954a289c603cab1b459a02
Source dataset
uspto-grants-2013_05
Patent number
US08445503B2

Linked notes

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