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

HRID 1915606Notes

Reaction equation

HRID 1915606 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 are 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 is heated to 130° C. by microwave irradiation under a inert gas atmosphere for 1 hour. 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 crude product is 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 are dried over sodium sulphate
  4. customthe solvent is evaporated
  5. customThe crude product is purified by chromatography on silica gel (dichloromethane/methanol)

Sources & evidence

ORD record
ord-2dd01baad6b044788f558b95c83517fa
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

Loading…