Water → HCID 57991135, compound

HRID 2091967Notes

Reaction equation

HRID 2091967 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.C(OC([N:16]([CH3:26])[C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)=O)(C)(C)C.[CH2:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[CH3:28].[OH2:34]>COCCOC>[CH3:26][NH:16][C:17]1[CH:18]=[CH:19][C:20]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:16][C:17]3[CH:18]=[CH:19][C:27]([N:29]4[CH2:32][CH2:33][O:34][CH2:31][CH2:30]4)=[CH:28][CH:22]=3)[N:7]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 45158885{4-[(tert-Butoxycarbonyl)(methyl)amino]phenyl}boronic acid

Product 1

HCID 57991135HCID 57991135, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A flask was charged with 2,4-dichloropyrimidine (810 mg, 5.5 mmol), 4-(tert-butoxycarbonyl(methyl)amino)phenylboronic acid B (4.93 g, 15 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocenepalladium (590 mg, 0.81 mmol, 15 mol %), triethylamine (1.8 mL, 13 mmol), and water (2 mL). Ethylene glycol dimethyl ether (5.0 mL) was added to the flask and the mixture was purged with N2. The reaction mixture was stirred under an N2 atmosphere at 90° C. for 1 hour, after which time, it was cooled to ambient temperature and filtered. The product, C, was isolated by removal of the solvent with a rotary evaporator and used without further purification. LCMS: m/z 319 (M+H)+.

Workup

  1. customthe mixture was purged with N2
  2. temperatureafter which time, it was cooled to ambient temperature
  3. filtrationfiltered
  4. customThe product, C, was isolated by removal of the solvent with a rotary evaporator
  5. customused without further purification

Sources & evidence

ORD record
ord-7a13cf740784496ab494112c7c0cab00
Source dataset
uspto-grants-2013_05
Patent number
US08440663B2

Reaction notes

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