Water → 5-Bromo-N-(4-methyl-3-nitrophenyl)pyrimidin-2-amine

HRID 2067877Notes

Reaction equation

HRID 2067877 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][C:11]=1[N+:17]([O-:19])=[O:18].CS(O)(=O)=O.O>O1CCOCC1>[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:14][C:13]2[CH:15]=[CH:16][C:10]([CH3:9])=[C:11]([N+:17]([O-:19])=[O:18])[CH:12]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 83904-Methyl-3-nitroanilineHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 638723175-Bromo-N-(4-methyl-3-nitrophenyl)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-Bromo-2-chloropyrimidine 4 (50 mmol), 4-methyl-3-nitroaniline (60 mmol) and methylsulphonic acid (15 mmol) are heated at reflux in 1,4-dioxane (100 mL) for 16 h. The mixture is poured into water, filtered and dried under vacuum to give 5-bromo-N-(4-methyl-3-nitrophenyl)pyrimidin-2-amine 27 as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 10.25 (s, 1H), 8.68 (s, 2H), 8.49 (d, J=2.0 Hz, 1H), 7.86 (dd, J=2.4, 8.4 Hz, 1H), 7.41 (d, J=8.4 Hz, 1H), 2.46 (s, 3H). MS (m/z) (M+1)+: 309.0, 311.0.

Workup

  1. filtrationfiltered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-d40a008442b6484da6f43e4d381155c7
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

Loading…