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

HRID 1887704Notes

Reaction equation

HRID 1887704 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[CH:4][N:3]=1.Cl.CN.C(Cl)CCl.C1C=CC2N(O)N=[N:24][C:22]=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]([NH:24][CH3:22])=[O:10])=[CH:6][N:5]=[CH:4][N:3]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 12014404-Aminopyrimidine-5-carboxylic acidHCID 6364545Methylamine hydrochloride

Product 1

HCID 134684384-amino-N-methylpyrimidine-5-carboxamideYield 85.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the mixture of 4-aminopyrimidine-5-carboxylic acid (0.75 g, 5.39 mmol), methylamine hydrogen chloride (0.44 g, 1.2 eq), EDC (1.67 g, 1.5 eq), HOBt (0.87 g, 1.2 eq) in DMF (20 mL) was added DIEA (3.8 mL, 4.0 eq). The mixture was stirred at room temperature overnight. The crude was concentrated and dissolved in EtOAc. It was washed with saturated NaHCO3 solution. The solvent was removed and the crude was purified by silica gel chromatography (0%˜20% MeOH/DCM) to obtain the desired product 4-amino-N-methylpyrimidine-5-carboxamide (0.701 g, isolated yield 85%).

Workup

  1. concentrationThe crude was concentrated
  2. dissolutiondissolved in EtOAc
  3. washIt was washed with saturated NaHCO3 solution
  4. customThe solvent was removed
  5. customthe crude was purified by silica gel chromatography (0%˜20% MeOH/DCM)

Sources & evidence

ORD record
ord-4fbe223b193d407082a56e5b2ff038b2
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

Loading…