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

HRID 1812081Notes

Reaction equation

HRID 1812081 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 C2H11ClN4O: 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-eb6ae1f87c7a44c6b3acc42618b8e19e
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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