Potassium Carbonate → 1,3,5-Triazin-2-amine, N,4-dicyclopropyl-6-(4-thiomorpholinyl)-

HRID 256708Notes

Reaction equation

HRID 256708 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[N:5]=[C:4]([NH:11][CH:12]2[CH2:14][CH2:13]2)[N:3]=1.[NH:15]1[CH2:20][CH2:19][S:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[CH:8]1([C:6]2[N:5]=[C:4]([NH:11][CH:12]3[CH2:14][CH2:13]3)[N:3]=[C:2]([N:15]3[CH2:20][CH2:19][S:18][CH2:17][CH2:16]3)[N:7]=2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67164ThiomorpholineHCID 18965200HCID 18965200, compound

Product 1

HCID 30733741,3,5-Triazin-2-amine, N,4-dicyclopropyl-6-(4-thiomorpholinyl)-Yield 83.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

12.2 g of 2-chloro-4-cyclopropyl-6-cyclopropylamino-1,3,5-triazine (0.057 mole), 5.97 g of thiomorpholine (0.057 mole) and 8 g of potassium carbonate (0.057 mole) are mixed in 100 ml of isopropyl alcohol and the mixture is heated at 75°-80° C. for 2 hours. It is cooled, the salts are filtered off and the filtrate is evaporated to dryness. The residue is taken up in 200 ml of dichloromethane, the solution is washed with water and dried over sodium sulfate and the solvent is evaporated. The product obtained is crystallized from a 1:2 (v/v) mixture of ethyl acetate-hexane to give 13.18 g of 2-cyclopropyl-4-cyclopropylamino-6-thiomorpholino-1,3,5-triazine. Yield: 83.5%. M.P.: 133°-134° C.

Workup

  1. temperaturethe mixture is heated at 75°-80° C. for 2 hours
  2. temperatureIt is cooled
  3. filtrationthe salts are filtered off
  4. customthe filtrate is evaporated to dryness
  5. washthe solution is washed with water
  6. dry with materialdried over sodium sulfate
  7. customthe solvent is evaporated
  8. customThe product obtained
  9. customis crystallized from a 1:2 (v/v) mixture of ethyl acetate-hexane

Sources & evidence

ORD record
ord-012ad8e3ad6243fd9a05aa24afe5e8e7
Source dataset
uspto-grants-1993_11
Patent number
US05258513

Reaction notes

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