Dichloromethane → HCID 178465299, compound

HRID 229364Notes

Reaction equation

HRID 229364 reaction equation
C[N:2]1[C:6]([CH3:7])=[N:5][C:4]([C:8]2[CH:13]=[CH:12][N:11]3[CH:14]=[C:15]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])[N:16]=[C:10]3[CH:9]=2)=[N:3]1.N1C=C(B(O)O)C=NC=1.C(=O)([O-])[O-].[Na+].[Na+].ClCCl>C(COC)OC.O.C(O)C.C(O)(=O)C>[CH2:21]([NH:20][C:18]([NH:17][C:15]1[N:16]=[C:10]2[CH:9]=[C:8]([C:4]3[NH:3][N:2]=[C:6]([CH3:7])[N:5]=3)[CH:13]=[CH:12][N:11]2[CH:14]=1)=[O:19])[CH3:22]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 11289559HCID 11289559, compound

Product 1

HCID 178465299HCID 178465299, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 5 (0.76 mmol), pyrimidine-5-boronic acid (0.105 g, 0.85 mmol), sodium carbonate (0.292 g, 2.75 mmol), and [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (0.007 g, 8.6 μmol) in 6 mL of 7:3:2 dimethoxyethane/water/ethanol was heated for 30 minutes at 80° C. in a CEM microwave reactor. The reaction was acidified with 2 mL glacial acetic acid and evaporated in vacuo. The residue was purified by silica gel chromatography (gradient elution 0-50% isopropanol in dichloromethane) to give the target compound (4). MS (APCI)=295.1 [M+H].

Workup

  1. customevaporated in vacuo
  2. customThe residue was purified by silica gel chromatography (gradient elution 0-50% isopropanol in dichloromethane)

Sources & evidence

ORD record
ord-bdf8372d3c7b4a5f9cf379f424c0377d
Source dataset
uspto-grants-2009_07
Patent number
US07563788B2

Reaction notes

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