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

HRID 368987노트

반응식

HRID 368987 반응식
[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

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 23284478HCID 23284478, 화합물HCID 178418573HCID 178418573, 화합물2회

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%.

후처리

  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)

출처 및 근거

ORD 기록
ord-66f5fcebc2604eafb93a61afc10561f9
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06136810

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