2-Methoxyethylamine → 4-Chloro-N-(2-methoxyethyl)-6-methyl-1,3,5-triazin-2-amine

HRID 1621669Notes

Reaction equation

HRID 1621669 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[Cl:6][C:7]1[N:12]=[C:11](Cl)[N:10]=[C:9]([CH3:14])[N:8]=1.CCN(C(C)C)C(C)C>O1CCOCC1>[Cl:6][C:7]1[N:8]=[C:9]([CH3:14])[N:10]=[C:11]([NH:5][CH2:4][CH2:3][O:2][CH3:1])[N:12]=1

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 160832,4-Dichloro-6-methyl-1,3,5-triazineHCID 81531Diisopropylethylamine

Product 1

HCID 866470584-Chloro-N-(2-methoxyethyl)-6-methyl-1,3,5-triazin-2-amineYield 31.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-methoxyethanamine (Aldrich, 0.350 g, 4.66 mmol) was added to a solution of 2,4-dichloro-6-methyl-1,3,5-triazine (0.80 g, 4.88 mmol) in dioxane (10 mL). Heat was generated. Hünig's base (1.0 mL, 5.73 mmol) was added and the mixture was stirred for 5 min. The mixture was partitioned between DCM (15 mL) and water. The organic phase was dried over Na2SO4 and concentrated. The resulting yellow oil was purified by chromatography on silica using EtOAc in hexane (20-80%) to give the desired product as a yellow solid (300 mg). LCMS (ES, pos.): calcd for C7H11ClN4O: 202.1. found: 203.0 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 5.93 (br. s., 1H); 3.60-3.70 (m, 2H); 3.49-3.58 (m, 2H); 3.38 (s, 3H); 2.42 (d, 3H).

Workup

  1. temperatureHeat
  2. customThe mixture was partitioned between DCM (15 mL) and water
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting yellow oil was purified by chromatography on silica

Sources & evidence

ORD record
ord-d59f3b863ef14c0c896f17b8b3dd4e31
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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