Dimethylamine → 2,4-Pyridinediamine, N(sup 4),N(sup 4),6-trimethyl-

HRID 1504778Notes

Reaction equation

HRID 1504778 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4](Cl)[CH:3]=1.[CH3:10][NH:11][CH3:12]>>[CH3:10][N:11]([CH3:12])[C:4]1[CH:5]=[C:6]([CH3:8])[N:7]=[C:2]([NH2:1])[CH:3]=1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 190505094-Chloro-6-methylpyridin-2-amine

Product 1

HCID 6675472,4-Pyridinediamine, N(sup 4),N(sup 4),6-trimethyl-

Conditions

Temperature
130 °C

Procedure

To 6-amino-4-chloro-2-picoline (500 mg, 3.51 mmol) in a vial under nitrogen was added dimethylamine (40% in water, 17.5 ml, 35.0 mmol). The reaction mixture was sealed and heated at 130° C. in a microwave for 2.5 hours. The reaction mixture was cooled, concentrated under reduced pressure, and purified by silica gel chromatography (2-10% methanol/DCM with 1% ammonium hydroxide, linear gradient) to give N4,N4,6-trimethylpyridine-2,4-diamine. MS ESI calc'd. for C8H14N3 [M+H]+ 152. found 152. 1H NMR (500 MHz, DMSO-d6) δ 6.15 (s, 2H), 6.02 (s, 1H), 5.54 (s, 1H), 2.90 (s, 6H), 2.18 (s, 3H).

Workup

  1. customThe reaction mixture was sealed
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure
  4. custompurified by silica gel chromatography (2-10% methanol/DCM with 1% ammonium hydroxide, linear gradient)

Sources & evidence

ORD record
ord-be7d9f75d3f14dc0aa52d055fcf08d76
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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