Sodium Carbonate → HCID 86630671, compound

HRID 1851199Notes

Reaction equation

HRID 1851199 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]2[N:14]=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=[C:4]2[N:3]=1.[CH:20]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)=[O:21].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.ClCCl.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]>[CH:17]([C:15]1[N:16]=[C:4]2[N:3]=[C:2]([C:25]3[CH:26]=[CH:27][C:22]([CH:20]=[O:21])=[CH:23][CH:24]=3)[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][N:5]2[N:14]=1)([CH3:19])[CH3:18]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 86630669HCID 86630669, compound

Product 1

HCID 86630671HCID 86630671, compound

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 5.30 g 5-chloro-2-isopropyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidine and 3.80 g 4-formylphenylboronic acid in 160 mL 1,2-dimethoxyethane were added 33 mL of a 10% w/w sodium carbonate solution and 0.71 g dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) and the resulting mixture was heated to 90° C. under an inert gas atmosphere for 18 h. The work up was performed by diluting the reaction mixture with water and dichloromethane, separating the phases and extraction of the aqueous phase with dichloromethane. The combined organic layers were dried over sodium sulphate, the solvent was evaporated and the residue suspended in ethyl acetate. The insoluble solid was filtered and the filtrate was evaporated. The residue was purified by chromatography on silica gel (dichloromethane/ethyl acetate) to yield the product.

Workup

  1. customseparating
  2. extractionthe phases and extraction of the aqueous phase with dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulphate
  4. customthe solvent was evaporated
  5. filtrationThe insoluble solid was filtered
  6. customthe filtrate was evaporated
  7. customThe residue was purified by chromatography on silica gel (dichloromethane/ethyl acetate)
  8. customto yield the product

Sources & evidence

ORD record
ord-6773057e553b46b8aa0214556000976b
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

Loading…