Formaldehyde → HCID 117775189, compound

HRID 2201558Notes

Reaction equation

HRID 2201558 reaction equation
[NH2:1][C:2]1[N:18]=[CH:17][C:16]([Br:19])=[CH:15][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)=[O:5].[OH-].[Na+].[CH2:22]=O>CCO>[Br:19][C:16]1[CH:17]=[N:18][C:2]2[NH:1][CH2:22][N:6]([CH2:7][C:8]3[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=3)[C:4](=[O:5])[C:3]=2[CH:15]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 55043537HCID 55043537, compound

Product 1

HCID 117775189HCID 117775189, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-amino-5-bromo-N-(4-fluorobenzyl)nicotinamide (200 mg, 0.62 mmol) and NaOH (50 mg, 1.23 mmol) in 10 mL of EtOH was added HCHO (1 mL, 37% in water) and then the mixture was heated at reflux for 30 minutes. After being concentrated in vacuo, the residue was suspended in water and extracted with EtOAc. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuo to give the crude product of 6-bromo-3-(4-fluorobenzyl)-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one (180 mg, yield: 87%) without further purification. 1H-NMR (CDCl3, 400 MHz) δ 8.28˜8.32 (m, 2H), 7.26˜7.31 (m, 2H), 7.02 (t, J=8.4 Hz, 2H), 5.01 (s, 2H), 4.68 (d, J=2.4 Hz, 2H). MS (M+H)+: 336/338.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. concentrationAfter being concentrated in vacuo
  4. extractionextracted with EtOAc
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df22b8145b654407899e1fb3b3afcebf
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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