Sodium Carbonate → 5-Bromo-4,6-dichloropyrimidin-2-amine

HRID 2401442Notes

Reaction equation

HRID 2401442 reaction equation
[Br:1]Br.[NH2:3][C:4]1[N:9]=[C:8]([Cl:10])[CH:7]=[C:6]([Cl:11])[N:5]=1.C(=O)([O-])[O-].[Na+].[Na+].CO.O>C(=O)(O)[O-].[Na+]>[Br:1][C:7]1[C:6]([Cl:11])=[N:5][C:4]([NH2:3])=[N:9][C:8]=1[Cl:10]

Participants

6

Reactant 4

HCID 10340Sodium Carbonate2×HCID 24408BromineHCID 655222-Amino-4,6-dichloropyrimidineHCID 22242641Methanol--water (1/1)

Product 1

HCID 6182885-Bromo-4,6-dichloropyrimidin-2-amineYield 83.7%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Bromine (0.85 mL, 0.0166 mole) was added dropwise over 20 minutes to a stirred suspension of 2-amino-4,6-dichloropyrimidine (CAS#56-05-3, 1.70 g, 0.01037 mole) and sodium carbonate (1.00 g, 0.01244 mole) in 1:1 methanol/water (30 mL) at ambient temperature. Ten minutes after the addition was complete, more sodium carbonate (0.78 g, 0.0093 mole) was added to the reaction mixture. The reaction mixture was stirred at ambient temperature for 42 hours, then it was diluted with aqueous sodium bicarbonate to provide 5-bromo-4,6-dichloropyrimidin-2-amine as a precipitate that was collected by filtration and rinsed with water. The vacuum-dried solid weighed 2.11 g (83.7% yield). 1H NMR (300 MHz, d6-DMSO) δ ppm 7.67 (s, 1H), 7.70 (s, 1H). MS (DCl—NH3) m/z=241 (M+H)+, m/z=258 (M+NH4)+.

Workup

  1. additionTen minutes after the addition

Sources & evidence

ORD record
ord-72ea0f280f184613afd083d3cafec1dc
Source dataset
uspto-grants-2014_08
Patent number
US08796297B2

Reaction notes

Loading…