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

HRID 1517437ノート

反応式

HRID 1517437 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4b5a421e92324505a837009abfae4496
出典データセット
uspto-grants-2012_07
特許番号
US08232278B2

反応ノート

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