Triethylamine → 5-bromo-N-ethyl-N-methylpyrimidine-2-carboxamide

HRID 1027703Notes

Reaction equation

HRID 1027703 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8](Cl)=[O:9])=[N:6][CH:7]=1.[CH2:11]([N:13](CC)[CH2:14]C)[CH3:12].C(NC)C>ClCCl>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([N:13]([CH2:11][CH3:12])[CH3:14])=[O:9])=[N:6][CH:7]=1

Participants

5

Procedure

5-Bromo-pyrimidine-2-carbonyl chloride (1600 mg, 7.225 mmol) was dissolved in dichloromethane (25 ml) and triethylamine (4.03 ml, 28.9 mmol) was added followed by ethyl-methyl-amine (0.68 mL, 7.92 mmol). The reaction was stirred at room temperature under nitrogen for 16 ours, after which time, LCMS indicated completion. The mixture was diluted with dichloromethane (50 ml) and washed with water (50 ml) followed by 10% citric acid (50 ml) and brine (50 ml). The organic layer was separated and dried over MgSO4, the residue was filtered and the solvent was removed in vacuo to afford the title compound 5-bromo-N-ethyl-N-methylpyrimidine-2-carboxamide (SM-3): (1.4 g, 79.4%) as a brown oil.

Workup

  1. washwashed with water (50 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationthe residue was filtered
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0c14297aed774874a82f544e3ae66413
Source dataset
uspto-grants-2014_05
Patent number
US08735396B2

Reaction notes

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