Dimethylamine → 5-bromo-4-methoxy-N,N-dimethylpyrimidin-2-amine

HRID 2410105Notes

Reaction equation

HRID 2410105 reaction equation
[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:11][NH:12][CH3:13]>C1COCC1>[Br:1][C:2]1[C:3]([O:9][CH3:10])=[N:4][C:5]([N:12]([CH3:13])[CH3:11])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 36631435-Bromo-2-chloro-4-methoxypyrimidine

Product 1

HCID 6158295-bromo-4-methoxy-N,N-dimethylpyrimidin-2-amineYield 94.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-bromo-2-chloro-4-methoxypyrimidine (3 g, 13.4 mmol) and dimethylamine (2 M in THF, 33.6 mL, 67.1 mmol) in THF (20 mL) was stirred for 18 h at rt and concentrated. The residue was purified by flash chromatography (hexane/EtOAc, 9:1) to afford 2.95 g of the title compound. tR: 1.04 min (LC-MS 2); ESI-MS: 232.0/234.0 [M+H]+ (LC-MS 2); Rf: 0.34 (hexane/EtOAc 9:1).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography (hexane/EtOAc, 9:1)

Sources & evidence

ORD record
ord-303821da64314ba085daad45ad2a8ad8
Source dataset
uspto-grants-2014_08
Patent number
US08815926B2

Reaction notes

Loading…