Sodium Carbonate → HCID 86696687, compound

HRID 1774189Notes

Reaction equation

HRID 1774189 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[F:7][C:8]1[C:9](B(O)O)=[CH:10][C:11]([O:14][CH3:15])=[N:12][CH:13]=1.[Cl:19][C:20]1[N:25]=[C:24](Cl)[CH:23]=[CH:22][N:21]=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]>[Cl:19][C:20]1[N:25]=[C:24]([C:9]2[C:8]([F:7])=[CH:13][N:12]=[C:11]([O:14][CH3:15])[CH:10]=2)[CH:23]=[CH:22][N:21]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 775312,4-DichloropyrimidineHCID 218864351,4-Dioxane--water (1/1)HCID 44754837(5-Fluoro-2-methoxypyridin-4-yl)boronic acid

Product 1

HCID 86696687HCID 86696687, compoundYield 100%

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 (1.6 g, 15 mmol) was added to 5-fluoro-2-methoxypyridin-4-ylboronic acid (1.0 g, 6.0 mmol) and 2,4-dichloropyrimidine (0.75 g, 5.0 mmol) in 4:1 dioxane/water (25 mL), and the suspension was purged with argon. PdCl2(dppf)*DCM (0.21 g, 0.25 mmol) was added, and the mixture was heated at 80° C. under argon overnight. The reaction mixture was diluted with water, and the resulting solid was collected by vacuum filtration, washed with water, and dried to provide the desired 2-chloro-4-(5-fluoro-2-methoxypyridin-4-yl)pyrimidine (1.2 g, 5.0 mmol, 99% yield) as a solid.

Workup

  1. customthe suspension was purged with argon
  2. filtrationthe resulting solid was collected by vacuum filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-018dba89c49347adba56e0ba3c9423c0
Source dataset
uspto-grants-2016_02
Patent number
US09259470B2

Reaction notes

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