Sodium Carbonate → HCID 86677062, 화합물

HRID 518256노트

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HRID 518256 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 86677062HCID 86677062, 화합물

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

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 μA, 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.

후처리

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

출처 및 근거

ORD 기록
ord-91527d9fd9c746b4b669f51c2032944c
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115141B2

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