Sodium Carbonate → HCID 58166641, compound

HRID 2366179Notes

Reaction equation

HRID 2366179 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[CH3:9][C:10]1(C)C(C)(C)OB(C=C)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:9]([C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1)=[CH2:10]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2380124-Amino-6-chloropyrimidineHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 58166641HCID 58166641, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-chloropyrimidin-4-amine (6.5 g, 0.050 mol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (9.24 g, 0.060 mol), tetrakis(triphenylphosphine)-palladium(0) (3.9 g, 0.0030 mol) and sodium carbonate (21 g, 0.20 mol) in dioxane (300 mL) and H2O (30 mL) was stirred at 90° C. under nitrogen for 15 hours. The mixture was concentrated under reduced pressure and the residue was partitioned between EtOAc (400 mL) and water (150 mL). The organic layer was separated, dried over Na2SO4, and concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with DCM/MeOH (20:1) to give the desired product as a white solid (4.8 g, 80% yield). LCMS (ESI) m/z: 122.1 [M+H+].

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between EtOAc (400 mL) and water (150 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography
  7. washeluting with DCM/MeOH (20:1)

Sources & evidence

ORD record
ord-31495645de444c7d8a1413a622605252
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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