Triethylamine → 2-Cyclopropylpyrimidin-4-amine

HRID 1786124Notes

Reaction equation

HRID 1786124 reaction equation
[CH2:1]1[CH:3]([C:4]([NH2:6])=[NH:5])[CH2:2]1.Cl.C(N(CC)CC)C.Cl[C:16](=[CH2:19])[C:17]#[N:18]>C(O)C>[CH:3]1([C:4]2[N:6]=[C:17]([NH2:18])[CH:16]=[CH:19][N:5]=2)[CH2:2][CH2:1]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 701982-ChloroacrylonitrileHCID 2781916Cyclopropanecarboximidamide hydrochloride

Product 1

HCID 450801122-Cyclopropylpyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cyclopropylcarbamidine hydrochloride (7.61 g) was dissolved in ethanol (125 mL) and triethylamine (19.35 mL) and 2-chloro-acrylonitrile (5.52 mL) were added. The resulting orange-yellow solution was refluxed for 30 minutes. The mixture was cooled and left in a refrigerator over night. The solid was removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (ethyl acetate/methanol 9:1) to give 2-cyclopropyl-pyrimidin-4-ylamine (4.2 g) as a light brown solid that was still contaminated with an unidentified component, but used without further purification. 1H NMR (δ, DMSO-d6, product signals only): 7.88 (d, 1H), 6.64 (br s, 2H), 6.16 (d, 1H), 1.89-1.82 (m, 1H), 0.87-0.81 (m, 4H).

Workup

  1. temperatureThe resulting orange-yellow solution was refluxed for 30 minutes
  2. temperatureThe mixture was cooled
  3. waitleft in a refrigerator over night
  4. customThe solid was removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by flash chromatography (ethyl acetate/methanol 9:1)

Sources & evidence

ORD record
ord-c04cd902f3dd427b9f372338b3870909
Source dataset
uspto-grants-2009_03
Patent number
US07507733B2

Reaction notes

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