Sodium Carbonate → HCID 86630684, compound

HRID 503774Notes

Reaction equation

HRID 503774 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([CH3:14])[N:5]2[N:15]=[C:16]([CH3:18])[N:17]=[C:4]2[N:3]=1.[CH:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:20].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]>[CH3:18][C:16]1[N:17]=[C:4]2[N:3]=[C:2]([C:24]3[CH:25]=[CH:26][C:21]([CH:19]=[O:20])=[CH:22][CH:23]=3)[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[C:6]([CH3:14])[N:5]2[N:15]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 86630683HCID 86630683, compound

Product 1

HCID 86630684HCID 86630684, 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
110 °C

Procedure

To a mixture of 1.25 g 5-chloro-2,7-dimethyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidine and 0.87 g 4-formylphenylboronic acid in 25 ml 1,2-dimethoxyethane are added 0.18 g dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct and 9.30 ml of a 10% w/w sodium carbonate solution. The resulting mixture is heated to 110° C. by microwave irradiation under an inert gas atmosphere for 45 min. 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 and the solvent is evaporated. The residue is purified by chromatography on silica gel (dichloromethane/methanol). The desired product is suspended in ethyl acetate/petrolether and isolated by filtration.

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. customThe residue is purified by chromatography on silica gel (dichloromethane/methanol)
  6. customisolated by filtration

Sources & evidence

ORD record
ord-dbf47bab519b42e4b272e29980da2e7e
Source dataset
uspto-grants-2010_08
Patent number
US07776864B2

Reaction notes

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