Triethylamine → 2-Cyclopropylpyrimidin-4-amine

HRID 1411767Notes

Reaction equation

HRID 1411767 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-amineYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cyclopropylcarbamidine hydrochloride (1.0 g, 8.3 mmol) was dissolved in ethanol (25 mL) and triethylamine (1.26 g, 12.5 mmol), followed by the addition of 2-chloroacrylo-nitrile (870 mg, 10 mmol). The resulting orange-yellow solution was refluxed for 1 h. The mixture was cooled to room temperature and filtered. The filtrate was concentrated in vacuo and the residue was purified by reverse-phase Combiflash to afford 196a (300 mg, 27%) as a light brown solid. MS-ESI: [M+H]+ 136

Workup

  1. temperatureThe resulting orange-yellow solution was refluxed for 1 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by reverse-phase Combiflash

Sources & evidence

ORD record
ord-ed08918dad4b4f02b0a8963b9ecdcb3c
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

Loading…