1,2-Dichloroethane → 5-Bromo-N-methylpyrimidine-4-carboxamide

HRID 58037Notes

Reaction equation

HRID 58037 reaction equation
[Br:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[N:6][CH:7]=1.C1C=CC2N(O)N=[N:17][C:15]=2C=1.C(Cl)CCl.Cl.CN.C(N(C(C)C)C(C)C)C>CN(C=O)C>[Br:1][C:2]1[C:3]([C:8]([NH:17][CH3:15])=[O:10])=[N:4][CH:5]=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 213292005-Bromopyrimidine-4-carboxylic acid

Product 1

HCID 838147435-Bromo-N-methylpyrimidine-4-carboxamideYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-bromopyrimidine-4-carboxylic acid (0.3 g, 1.478 mmol) in DMF (3 mL) were added HOBt (0.260 g, 1.921 mmol), EDC (0.397 g, 2.069 mmol), methanamine HCl (0.200 g, 2.96 mmol), followed by N-ethyl-N-isopropylpropan-2-amine (0.772 mL, 4.43 mmol). The reaction mixture was stirred for 18 hours at room temperature. The crude residue was purified by preparative HPLC (Waters SunFire C18, 5 μm, 30 mm ID×75 mm column) eluting with 5% ACN (containing 0.035% TFA) in water (containing 0.05% TFA) to give the title compound as a light brown solid (0.11 g, 35%). ESI-MS m/z [M+H]+ calc'd for C6H7BrN3O, 216.0. found 216.0.

Workup

  1. customThe crude residue was purified by preparative HPLC (Waters SunFire C18, 5 μm, 30 mm ID×75 mm column)
  2. washeluting with 5% ACN (containing 0.035% TFA) in water (containing 0.05% TFA)

Sources & evidence

ORD record
ord-055340dfd0d44bdf8f11f2c55eb6e549
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Reaction notes

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