Ethyl 1-methylcyclopropanecarboxylate → 1,3,5-Triazin-2-amine, N-cyclopropyl-4-(1-methylcyclopropyl)-6-(4-morpholinyl)-

HRID 256713Notes

Reaction equation

HRID 256713 reaction equation
[Na].Cl.[NH:3]=[C:4]([NH:14][CH:15]1[CH2:17][CH2:16]1)[NH:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[NH:7].[CH3:18][C:19]1([C:22](OCC)=O)[CH2:21][CH2:20]1>C(O)C>[CH:15]1([NH:14][C:4]2[N:3]=[C:18]([C:19]3([CH3:22])[CH2:21][CH2:20]3)[N:7]=[C:6]([N:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[N:5]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 544234Ethyl 1-methylcyclopropanecarboxylateHCID 5360545SodiumHCID 178479355N'-(N'-cyclopropylcarbamimidoyl)morpholine-4-carboximidamide;hydrochloride

Product 1

HCID 30733791,3,5-Triazin-2-amine, N-cyclopropyl-4-(1-methylcyclopropyl)-6-(4-morpholinyl)-Yield 17.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

0.48 g (20 mmoles) of sodium is dissolved in 20 ml of anhydrous ethanol. This solution is added to an ethanol solution containing 2.48 g (10 mmoles) of N-[imino(cyclopropylamino)methyl]-4-morpholinecarboximidamide hydrochloride, and 2.82 g (22 mmoles) of ethyl 1-methylcyclopropane-carboxylate are then also added to the mixture. The mixture is then heated under reflux under nitrogen for 88 hours. It is cooled, the alcohol is evaporated under reduced pressure and the residue is redissolved in 50 ml of water and 200 ml of dichloromethane. The aqueous phase is separated off and the organic phase is washed twice with 50 ml of water and dried over magnesium sulfate. The solvent is evaporated under reduced pressure and the residue is recrystallized from a 1:1 (v/v) mixture of petroleum ether-dichloromethane. 0.49 g of 2-cyclopropylamino-4-(1-methylcyclopropyl)-6-morpholino-1,3,5-triazine is obtained. Yield: 17%. M.P.: 94°-95°% C.

Workup

  1. additionare then also added to the mixture
  2. temperatureThe mixture is then heated
  3. temperatureunder reflux under nitrogen for 88 hours
  4. temperatureIt is cooled
  5. customthe alcohol is evaporated under reduced pressure
  6. dissolutionthe residue is redissolved in 50 ml of water
  7. customThe aqueous phase is separated off
  8. washthe organic phase is washed twice with 50 ml of water
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent is evaporated under reduced pressure
  11. customthe residue is recrystallized from a 1:1 (v/v) mixture of petroleum ether-dichloromethane

Sources & evidence

ORD record
ord-df6d0c6989794214b23631a19d754956
Source dataset
uspto-grants-1993_11
Patent number
US05258513

Reaction notes

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