Sodium Carbonate → HCID 86677062、化合物

HRID 1626925ノート

反応式

HRID 1626925 の反応式
[Cl:1][C:2]1[C:7](I)=[CH:6][N:5]=[C:4]([NH2:9])[N:3]=1.[N:10]1[CH:15]=[CH:14][CH:13]=[C:12](B(O)O)[CH:11]=1.B(O)O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[Cl:1][C:2]1[C:7]([C:12]2[CH:11]=[N:10][CH:15]=[CH:14][CH:13]=2)=[CH:6][N:5]=[C:4]([NH2:9])[N:3]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 61668Boronic AcidHCID 27343783-Pyridinylboronic acidHCID 582999524-chloro-5-iodopyriMidin-2-aMine

生成物 1

HCID 86677062HCID 86677062、化合物

試薬・触媒・溶媒 2

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

反応条件

温度
90 °C

実験手順

4-Chloro-5-(pyridin-3-yl)pyrimidin-2-amine 131 was prepared from the coupling of 4-chloro-5-iodopyrimidin-2-amine with pyridin-3-ylboronic acid as follows: the amine (150 mg, 0.587 mmol), and the boronic acid (144 mg, 1.174 mmol) were suspended in dioxane (2.5 mL) and Na2CO3 (783 μl, 1.174 mmol). The mixture was bubbled with Ar for 5 min then charged with Pd(Ph3P)4 (136 mg, 0.117 mmol). The mixture was stirred at 90° C. for 2 h, then cooled to room temperature. The mixture was partitioned between EtOAc and water. The organic layer was dried, filtered, and concentrated to give a residue which was purified by silica gel column chromatography to give 4-chloro-5-(pyridin-3-yl)pyrimidin-2-amine 131.

後処理

  1. customThe mixture was bubbled with Ar for 5 min
  2. temperaturecooled to room temperature
  3. customThe mixture was partitioned between EtOAc and water
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue which
  8. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-bf88f98f51a84a3295e8f7830d30bb11
出典データセット
uspto-grants-2014_07
特許番号
US08785470B2

反応ノート

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