Bis(2-Methoxyethyl)amine → N4,N4-bis(2-methoxyethyl)pyrimidine-4,6-diamine

HRID 1241366Notes

Reaction equation

HRID 1241366 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:18][O:19][CH2:20][CH2:21][NH:22][CH2:23][CH2:24][O:25][CH3:26]>C(O)CCC>[CH3:18][O:19][CH2:20][CH2:21][N:22]([CH2:23][CH2:24][O:25][CH3:26])[C:2]1[CH:3]=[C:4]([NH2:8])[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 2383Bis(2-Methoxyethyl)amineHCID 81531DiisopropylethylamineHCID 2380124-Amino-6-chloropyrimidine

Product 1

HCID 21934632N4,N4-bis(2-methoxyethyl)pyrimidine-4,6-diamine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
180 °C

Procedure

6-Chloropyrimidin-4-amine 7-2 (0.3 g, 2.32 mmol) and diisopropylethylamine (0.30 g, 2.32 mmol) were suspended in n-butanol and then 2-methoxy-N-(2-methoxyethyl)ethanamine 6-1 (0.31 g, 2.32 mmol) was added. The reaction was stirred at 180° C. for 24 hours. The solvent was removed under reduced pressure and the product 6-2 was purified on a silica column. 1H-NMR (DMSO): 7.91 ppm (s, 1H); 6.10 ppm (2H); 5.51 ppm (s, 1H); 3.45 ppm (m, 4H); 3.45 ppm (m, 4H); 3.25 ppm (s, 6H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe product 6-2 was purified on a silica column

Sources & evidence

ORD record
ord-b68a349e9d414c65a5f2d3c72e45bfc8
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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