Methanol → HCID 68699731, compound

HRID 1624885Notes

Reaction equation

HRID 1624885 reaction equation
[CH2:1]([N:4]1[C:9](=[O:10])[C:8](Br)=[N:7][N:6]([C:12]2[CH:13]=[C:14]([NH:18][C:19](=[O:21])[CH3:20])[CH:15]=[CH:16][CH:17]=2)[C:5]1=[O:22])[CH:2]=[CH2:3].[Na].[CH3:24][OH:25]>>[CH2:1]([N:4]1[C:9](=[O:10])[C:8]([O:25][CH3:24])=[N:7][N:6]([C:12]2[CH:13]=[C:14]([NH:18][C:19](=[O:21])[CH3:20])[CH:15]=[CH:16][CH:17]=2)[C:5]1=[O:22])[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 5360545SodiumHCID 68701529HCID 68701529, compound

Product 1

HCID 68699731HCID 68699731, compoundYield 86%

Procedure

According to Scheme 3 Step 3: To a solution of compound 6(B) (800 mg, 2.19 mmol) in MeOH (10 mL) was added. a solution of sodium methoxyde 2M in methanol (1.1 mL, 2.19 mol). After 1 h of stirring at room temperature, the mixture was quenched with water and extracted with ethyl acetate (×3). The combined organic layers were successively washed with water, brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude solid was purified by flash chromatography with silica gel (Merck Flashmart prepacked column 10 g SiO2) using CH2Cl2/MeOH 98/2 as eluant to afford N-(3-(4-allyl-6-methoxy-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide 6(C) (600 mg, 86%) as a white solid.

Workup

  1. customthe mixture was quenched with water
  2. extractionextracted with ethyl acetate (×3)
  3. washThe combined organic layers were successively washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude solid was purified by flash chromatography with silica gel (Merck Flashmart prepacked column 10 g SiO2)

Sources & evidence

ORD record
ord-ee84c706bc074072b59cb0b1c4982dda
Source dataset
uspto-grants-2014_07
Patent number
US08779129B2

Reaction notes

Loading…