Sodium Carbonate → HCID 86630671, compound

HRID 1915559Notes

Reaction equation

HRID 1915559 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 are 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 is heated to 90° C. under an inert gas atmosphere for 18 h. The work up is 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 are dried over sodium sulphate, the solvent is evaporated and the residue suspended in ethyl acetate. The insoluble solid is filtered and the filtrate is evaporated. The residue is 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 are dried over sodium sulphate
  4. customthe solvent is evaporated
  5. filtrationThe insoluble solid is filtered
  6. customthe filtrate is evaporated
  7. customThe residue is purified by chromatography on silica gel (dichloromethane/ethyl acetate)
  8. customto yield the product

Sources & evidence

ORD record
ord-f1e0ed52aa354e329a1628203771699d
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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