Sodium Carbonate → HCID 86677062, compound

HRID 1626925Notes

Reaction equation

HRID 1626925 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

HCID 86677062HCID 86677062, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bf88f98f51a84a3295e8f7830d30bb11
Source dataset
uspto-grants-2014_07
Patent number
US08785470B2

Reaction notes

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