1,2-Dimethoxyethane → 4-(2-chloropyrimidin-4-yl)-N,N-dimethylaniline

HRID 470317Notes

Reaction equation

HRID 470317 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[Cl:13][C:14]1[N:19]=[C:18](Cl)[CH:17]=[CH:16][N:15]=1.C([O-])([O-])=O.[Na+].[Na+].C(COC)OC>O>[Cl:13][C:14]1[N:19]=[C:18]([C:6]2[CH:7]=[CH:8][C:3]([N:2]([CH3:12])[CH3:1])=[CH:4][CH:5]=2)[CH:17]=[CH:16][N:15]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 775312,4-DichloropyrimidineHCID 27343444-(Dimethylamino)phenylboronic acid

Product 1

HCID 534858024-(2-chloropyrimidin-4-yl)-N,N-dimethylanilineYield 78.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-dimethylaminophenyl boronic acid (10 g, 60.6 mM), 2,4-dichloropyrimidine (9 g, 60.4 mM), Na2CO3 (12 g, 114.2 mM), tetrakistriphenylphosphine palladium (2.5 g, 2.1 mM), dimethoxyethane (120 ml) and water (35 ml) was heated at 80° C. under a nitrogen atmosphere for 16 hr. The reaction was cooled in an ice bath and the resulting yellow suspension was filtered and the solid washed with water (3×50 ml) then ethyl acetate (2×50 ml). The solid was dried in vaccuo to afford [4-(2-Chloro-pyrimidin-4-yl)-phenyl]-dimethyl-amine (11.1 g, 78% yield) as an orange solid. ES-MS MH+234, 236, 1H NMR (300 MHz, ppm, DMSO-d6): 8.57 (d, 1H), 8.05 (d, 2H), 7.92 (d, 1H), 6.80 (d, 1H), 3.03 (s, 6H)

Workup

  1. temperatureThe reaction was cooled in an ice bath
  2. filtrationthe resulting yellow suspension was filtered
  3. washthe solid washed with water (3×50 ml)
  4. customThe solid was dried in vaccuo

Sources & evidence

ORD record
ord-485c2412996649b1815afdd98fa35327
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

Loading…