Sodium Methoxide → HCID 68825442, compound

HRID 657114Notes

Reaction equation

HRID 657114 reaction equation
Cl[C:2]1[C:3]2[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:4]=2[N:5]=[C:6](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]=1.[CH3:21][O-:22].[Na+]>CO>[CH3:21][O:22][C:2]1[C:3]2[CH2:19][CH2:18][C:17](=[O:20])[NH:16][C:4]=2[N:5]=[C:6](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 57928091HCID 57928091, compound

Product 1

HCID 68825442HCID 68825442, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 4-chloro-2-[(E)-2-phenylethenyl]-5,8-dihydropyrido[2,3-d]pyrimidin-7(6H)-one (0.45 g, 1.58 mmol) in MeOH (10 mL) was added NaOMe (0.094 g, 1.74 mmol). The reaction mixture was heated at reflux for 3 h, at which time an additional 0.10 g NaOMe was added and refluxing was continued. This was repeated two more times over 9 h. After the disappearance of all starting material (LCMS), the reaction was concentrated onto silica gel and purified by column chromatography (silica gel) using a DCM/DCM-MeOH—NH4OH (90:10:1) gradient to yield the desired product as an off-white solid (0.404 g, 91%).

Workup

  1. temperatureThe reaction mixture was heated
  2. additionwas added
  3. temperaturerefluxing
  4. customover 9 h
  5. concentrationAfter the disappearance of all starting material (LCMS), the reaction was concentrated onto silica gel
  6. custompurified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-9cb856756c2b4f79bbcfc63982e0935e
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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