Hydrochloric Acid → 6-Chloro-2-imino-N-methyl-N-phenyl-1,2-dihydropyrimidin-4-amine

HRID 2367374Notes

Reaction equation

HRID 2367374 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:10]1[CH:15]=[C:14]([Cl:16])[N:13]=[C:12]([NH2:17])[N:11]=1.Cl>O1CCOCC1>[Cl:16][C:14]1[N:13]=[C:12]([NH2:17])[N:11]=[C:10]([N:2]([CH3:1])[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7515N-MethylanilineHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 2387466-Chloro-2-imino-N-methyl-N-phenyl-1,2-dihydropyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 20-mL screw-cap vial was charged with N-methylaniline (0.653 g, 6.1 mmol), 4,6-dichloro-2-pyrimidinamine (1 g, 6.1 mmol), 1,4-dioxane (5 mL), and HCl (0.152 mL, 0.61 mmol, 4M in 1,4-dioxane). The vial was capped and stirred at reflux overnight. At this time, LCMS analysis indicated good conversion to the desired product, so the reaction mixture was poured into 1:1 NaHCO3 (sat) and water (20 mL) and extracted with EtOAc (3×50 mL). The combined organics were dried (Na2SO4) and concentrated. The solid residue was triturated with CH2Cl2, to yield the title compound (644 mg) as an off-white solid. LC-MS (ES) m/z=235 [M+H]+.

Workup

  1. customA 20-mL screw-cap vial
  2. customThe vial was capped
  3. temperatureat reflux overnight

Sources & evidence

ORD record
ord-5d8d730efd6b4ba8a9a9547bd6214134
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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