Acetic Acid → 6-(4-Fluorophenyl)pyrido[3,2-d]pyrimidin-4(1H)-one

HRID 1517437노트

반응식

HRID 1517437 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]=[CH:7][NH:8][C:9](=[O:12])[C:10]=2[N:11]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].C(O)(=O)C>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]=[CH:7][NH:8][C:9](=[O:12])[C:10]=3[N:11]=2)=[CH:16][CH:15]=1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 1354270966-Chloropyrido[3,2-d]pyrimidin-4(3H)-one

생성물 1

HCID 1360008906-(4-Fluorophenyl)pyrido[3,2-d]pyrimidin-4(1H)-one수율 90.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of 6-chloro-pyrido[3,2-d]pyrimidin-4(3H)one (1.0 g, 5.5 mmol) in dioxane (80 ml) and water (20 ml) was added 4-fluorophenylboronic acid (770 mg, 5.5 mmol), K2CO3 (2.28 g, 16.5 mmol), and tetrakis(triphenylphosphine)palladium(0) (290 mg, 0.25 mmol). The mixture was heated at reflux for 20 hours. After cooling to room temperature, the reaction mixture was neutralized to pH 5-6 with acetic acid, concentrated to a small volume, filtered and washed with water to yield a crude product. The crude residue was purified by silica gel flash chromatography, the mobile phase being a mixture of methanol and dichloromethane, in a volume ratio of 1:30, yielding the title compound as a white solid (1.2 g, yield: 90%) which was characterised by its mass spectrum as follows: MS (m/z): 242 ([M+H]+, 100).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 20 hours
  3. concentrationconcentrated to a small volume
  4. filtrationfiltered
  5. washwashed with water
  6. customto yield a crude product
  7. customThe crude residue was purified by silica gel flash chromatography
  8. additiona mixture of methanol and dichloromethane

출처 및 근거

ORD 기록
ord-4b5a421e92324505a837009abfae4496
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232278B2

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