Ammonium Chloride → 4-(3-chlorophenyl)-1-ethyl-7-(1-hydroxyethyl)pyrido[2,3-d]pyrimidin-2(1H)-one

HRID 368987Notes

Reaction equation

HRID 368987 reaction equation
[CH3:1][Mg]Br.[Cl:4][C:5]1[CH:6]=[C:7]([C:11]2[C:12]3[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[N:20][C:13]=3[N:14]([CH2:18][CH3:19])[C:15](=[O:17])[N:16]=2)[CH:8]=[CH:9][CH:10]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:4][C:5]1[CH:6]=[C:7]([C:11]2[C:12]3[CH:23]=[CH:22][C:21]([CH:24]([OH:25])[CH3:1])=[N:20][C:13]=3[N:14]([CH2:18][CH3:19])[C:15](=[O:17])[N:16]=2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23284478HCID 23284478, compoundHCID 178418573HCID 178418573, compound2×

Product 1

HCID 232844934-(3-chlorophenyl)-1-ethyl-7-(1-hydroxyethyl)pyrido[2,3-d]pyrimidin-2(1H)-oneYield 30.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 M Methylmagnesium bromide (14 ml, 14 mmol) was added to a solution of 4.4 g (14 mmol) of 4-(3-chlorophenyl)-1-ethylpyrido[2,3-d]pyrimidin-2(1H)-one-7-carbaldehyde in 50 ml of tetrahydrofuran under ice-cooling, followed by stirring for 30 minutes under ice-cooling. Then, 7 ml (7 mmol) of 1 M methylmagnesium bromide was added and the mixture was stirred for 30 minutes under ice-cooling. Then, saturated ammonium chloride aqueous solution was added, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate, magnesium sulfate was removed by filtration and the resulting filtrate was concentrated under a reduced pressure. Thereafter, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate-chloroform) to give 1.4 g of 4-(3-chlorophenyl)-1-ethyl-7-(1-hydroxyethyl)pyrido[2,3-d]pyrimidin-2(1H)-one. The yield was 30%.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred for 30 minutes under ice-
  4. temperaturecooling
  5. extractionfollowed by extraction with chloroform
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate, magnesium sulfate
  7. customwas removed by filtration
  8. concentrationthe resulting filtrate was concentrated under a reduced pressure
  9. customThereafter, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate-chloroform)

Sources & evidence

ORD record
ord-66f5fcebc2604eafb93a61afc10561f9
Source dataset
uspto-grants-2000_10
Patent number
US06136810

Reaction notes

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