Sodium Carbonate → 4-[7-(Dimethylamino)-2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]benzaldehyde

HRID 1851226Notes

Reaction equation

HRID 1851226 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([N:14]([CH3:16])[CH3:15])[N:5]2[N:17]=[C:18]([CH3:20])[N:19]=[C:4]2[N:3]=1.[CH:21]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)=[O:22].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]>[CH3:15][N:14]([CH3:16])[C:6]1[N:5]2[N:17]=[C:18]([CH3:20])[N:19]=[C:4]2[N:3]=[C:2]([C:26]2[CH:27]=[CH:28][C:23]([CH:21]=[O:22])=[CH:24][CH:25]=2)[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 866306975-Chloro-N,N,2-trimethyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

Product 1

HCID 866306984-[7-(Dimethylamino)-2-methyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]benzaldehyde

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
130 °C

Procedure

To a mixture of 370 mg 5-chloro-N,N,2-trimethyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine and 231 mg 4-formylphenylboronic acid in 7 mL 1,2-dimethoxyethane were added 2.5 mL of a 10% w/w sodium carbonate solution and 47 mg dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II). The resulting mixture was heated to 130° C. by microwave irradiation under a inert gas atmosphere for 1 hour. 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 and the solvent was evaporated. The crude product was purified by chromatography on silica gel (dichloromethane/methanol) to yield the desired 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. customThe crude product was purified by chromatography on silica gel (dichloromethane/methanol)

Sources & evidence

ORD record
ord-89a4e4b25f16403a91a26d3bcbc387a0
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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