3-Nitrophenylboronic Acid → HCID 69560024, compound

HRID 1796094Notes

Reaction equation

HRID 1796094 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][C:15]([C:17]([CH3:27])([O:19][Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH3:18])=[N:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[N+:28]([C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1)([O-:30])=[O:29]>C1COCC1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:18][C:17]([C:15]1[CH:14]=[CH:13][N:12]2[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([C:35]4[CH:34]=[CH:33][CH:32]=[C:31]([N+:28]([O-:30])=[O:29])[CH:36]=4)[N:7]=3)=[CH:9][N:10]=[C:11]2[N:16]=1)([O:19][Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH3:27]

Participants

7

Reactant 2

HCID 16773-Nitrophenylboronic AcidHCID 878895493-(2-Chloropyrimidin-4-yl)-7-(1-methyl-1-triethylsilanyloxyethyl)-imidazo[1,2-alpha]pyrimidine

Product 1

HCID 69560024HCID 69560024, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 3-(2-chloropyrimidin-4-yl)-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine (prepared according to Example 34) (250 mg, 0.62 mmol), 3-nitrobenzeneboronic acid (207 mg, 1.24 mmol) and tetrakis(triphenylphosphine)palladium(0) (71 mg, 10 mol %) in THF (3 ml) and 2N Na2CO3 solution (1.24 ml, 2.48 mnmol) was heated at reflux for 2.5 h. The mixture was cooled to room temperature, diluted with CH2Cl2 (30 ml), separated and concentrated to approximately 2 ml under reduced pressure. Purification by column chromatography on silica using 3% MeOH/CH2Cl2 afforded 7-(1-methyl-1-triethylsilanyloxyethyl)-3-[2-(3-nitrophenyl)pyrimidin-4-yl]imidazo[1,2-α]pyrimidine: m/z (ES+) 491 (M+H+).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 h
  3. customseparated
  4. concentrationconcentrated to approximately 2 ml under reduced pressure
  5. customPurification by column chromatography on silica using 3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-05b8f5f3a2704d4face78a81d24edc86
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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