Sodium Carbonate → HCID 86696661, compound

HRID 2365808Notes

Reaction equation

HRID 2365808 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[F:7][C:8]1[CH:13]=[C:12](B(O)O)[CH:11]=[CH:10][N:9]=1.Cl[C:18]1[N:23]=[CH:22][N:21]=[C:20]([NH:24][CH:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[CH:19]=1.O1CCOCC1.O>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:7][C:8]1[CH:13]=[C:12]([C:18]2[N:23]=[CH:22][N:21]=[C:20]([NH:24][CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:19]=2)[CH:11]=[CH:10][N:9]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27833962-Fluoropyridine-4-boronic acidHCID 218864351,4-Dioxane--water (1/1)HCID 61279786HCID 61279786, compound

Product 1

HCID 86696661HCID 86696661, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Sodium carbonate (4.24 g, 40.0 mmol) was added to 2-fluoropyridin-4-ylboronic acid (2.26 g, 16.0 mmol) and 6-chloro-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine (2.85 g, 13.3 mmol) in 4:1 dioxane/water (100 mL), and the suspension was purged with argon. PdCl2(dppf)*DCM (0.545 g, 0.667 mmol) was added, and the mixture was heated at 80° C. under nitrogen. After agitating for 6 hours, the reaction mixture was cooled, diluted with water and extracted with ethyl acetate two times. The extract was washed with water, brine, dried and evaporated. Purified by chromatography on silica gel, eluted with 50-70% ethyl acetate/hexane to give 6-(2-fluoropyridin-4-yl)-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine (2.50 g, 9.11 mmol, 68.3% yield) as a solid.

Workup

  1. customthe suspension was purged with argon
  2. temperaturethe reaction mixture was cooled
  3. extractionextracted with ethyl acetate two times
  4. washThe extract was washed with water, brine
  5. customdried
  6. customevaporated
  7. customPurified by chromatography on silica gel
  8. washeluted with 50-70% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ba0181cbad7e43098893a01407e5df6b
Source dataset
uspto-grants-2014_04
Patent number
US08697715B2

Reaction notes

Loading…