Ammonia → (R)-1-[2-(2, 3-methylenedioxyphenyl) heptyl]-3-[4, 6-bis (dimethylamino) pyrimidine-5-yl]urea

HRID 1756783Notes

Reaction equation

HRID 1756783 reaction equation
[NH2:1][C:2]1[C:3]([N:11]([CH3:13])[CH3:12])=[N:4][CH:5]=[N:6][C:7]=1[N:8]([CH3:10])[CH3:9].[C:14](=O)(OC(Cl)(Cl)Cl)[O:15]C(Cl)(Cl)Cl.C(N(CC)CC)C.[CH2:33]1[O:41][C:40]2[C:35](=[C:36]([C@@H:42]([CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:43][NH2:44])[CH:37]=[CH:38][CH:39]=2)[O:34]1.N>C(Cl)Cl.O>[CH2:33]1[O:41][C:40]2[C:35](=[C:36]([C@@H:42]([CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:43][NH:44][C:14]([NH:1][C:2]3[C:3]([N:11]([CH3:13])[CH3:12])=[N:4][CH:5]=[N:6][C:7]=3[N:8]([CH3:9])[CH3:10])=[O:15])[CH:37]=[CH:38][CH:39]=2)[O:34]1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 8471TriethylamineHCID 94429Triphosgene2×HCID 10331642(R)-2-(2, 3-methylenedioxyphenyl) heptylamineHCID 155853705-Amino-4,6-bis(dimethylamino)pyrimidine

Product 1

HCID 53983223(R)-1-[2-(2, 3-methylenedioxyphenyl) heptyl]-3-[4, 6-bis (dimethylamino) pyrimidine-5-yl]ureaYield 158.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 23.78 g (0.1405 mol) of 5-amino-4, 6-bis (dimethylamino) pyrimidine in 476 ml of methylene chloride were added 17.4 g (0.0586 mol) of bis(trichloromethyl) carbonate (namely triphosgene) and 34.1 g (0.337 mol) of triethylamine, and the resultant mixture was refluxed with heating for 1.5 hours. The reaction mixture was allowed to cool at room temperature, mixed with 33.0 g (0.1402 mol) of (R)-2-(2, 3-methylenedioxyphenyl)-heptylamine and allowed to react at room temperature overnight. The reaction mixture was mixed with a small amount of aqueous ammonia and water, and the aqueous layer was extracted with methylene chloride. The organic layer was washed with water, dried over anhydrous magnesium sulfate and the solvent evaporated. The residue was chromatographed on a silica gel column, eluting with chloroform-1% methanol/chloroform-2% methanol/chloroform and recrystallized from heptane and ethyl acetate to give 41.0 g of the titled compound.

Workup

  1. temperaturewith heating for 1.5 hours
  2. customto react at room temperature overnight
  3. extractionthe aqueous layer was extracted with methylene chloride
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent evaporated
  7. customThe residue was chromatographed on a silica gel column
  8. washeluting with chloroform-1% methanol/chloroform-2% methanol/chloroform
  9. customrecrystallized from heptane and ethyl acetate

Sources & evidence

ORD record
ord-9cd4281626324965b931d723783289a9
Source dataset
uspto-grants-1995_08
Patent number
US05442060

Reaction notes

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