Diethylamine → 2,6-Dichloro-N,N-diethylpyrimidin-4-amine

HRID 2074079Notes

Reaction equation

HRID 2074079 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[CH2:10]([NH:12][CH2:13][CH3:14])[CH3:11].C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[N:3]=[C:4]([N:12]([CH2:13][CH3:14])[CH2:10][CH3:11])[CH:5]=[C:6]([Cl:8])[N:7]=1

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 8471TriethylamineHCID 773782,4,6-Trichloropyrimidine

Product 1

HCID 534229742,6-Dichloro-N,N-diethylpyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of 2.0 g (10.90 mmols) of 2,4,6-trichloropyrimidine in 25 mL of anhydrous ethanol at 0° C., was added drop wise a solution 0.79 g (10.90 mmols) of diethylamine in 5 mL of ethanol. This was followed by the addition of 2.3 mL (16.35 mmols) of triethylamine and the mixture was stirred for further 30 min. The mixture was then concentrated and 25 mL of CH2Cl2 and 25 mL of water were added. The organic layer was separated and the aqueous layer was extracted by additional amount of dichloromethane (2×10 mL) and the extracts were combined, dried over anhydrous Na2SO4 and concentrated. Column chromatography on silica gel afforded 1.48 g (62%) of L as colorless solid.

Workup

  1. concentrationThe mixture was then concentrated
  2. addition25 mL of CH2Cl2 and 25 mL of water were added
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted by additional amount of dichloromethane (2×10 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customColumn chromatography on silica gel afforded 1.48 g (62%) of L as colorless solid

Sources & evidence

ORD record
ord-e56fe79a6b7b4ec4b73f4b164cfe0b89
Source dataset
uspto-grants-2011_04
Patent number
US07919487B2

Reaction notes

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