Dimethylamine → 6-Chloro-N~4~,N~4~-dimethylpyrimidine-2,4-diamine

HRID 2367206Notes

Reaction equation

HRID 2367206 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.C[CH2:11][N:12](C(C)C)[CH:13](C)C.CNC.O>C(#N)C>[Cl:8][C:6]1[N:5]=[C:4]([NH2:9])[N:3]=[C:2]([N:12]([CH3:13])[CH3:11])[CH:7]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 655222-Amino-4,6-dichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 2517356-Chloro-N~4~,N~4~-dimethylpyrimidine-2,4-diamineYield 104.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4,6-dichloropyrimidinamine (2.0 g, 12.2 mmol) in acetonitrile were added Hunig's base (2.34 mL, 13.4 mmol) and dimethylamine (6.7 mL, 13.4 mmol), and the reaction mixture was stirred for 1.5 hours at 50° C. The mixture was poured onto CH2Cl2 and water. The organic layer was separated, washed with brine, and concentrated to afford the title compound (2.2 g, 94%) as an off-white solid. LC-MS (ES) m/z=173, 175 [M+H]+.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a5fe065f3c5d445ebd92851879f58e35
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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