1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → 5-(2-Phthalimidoethylamino)-1,3,6-trimethylpyrimidine-2,4(1H,3H)-dione

HRID 365183Notes

Reaction equation

HRID 365183 reaction equation
[NH2:1][C:2]1[C:3](=[O:12])[N:4]([CH3:11])[C:5](=[O:10])[N:6]([CH3:9])[C:7]=1[CH3:8].Br[CH2:14][CH2:15][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:17]1(=[O:26])[N:16]([CH2:15][CH2:14][NH:1][C:2]2[C:3](=[O:12])[N:4]([CH3:11])[C:5](=[O:10])[N:6]([CH3:9])[C:7]=2[CH3:8])[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]12

Participants

5

Reactant 3

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 816935AB-323/25048145

Product 1

HCID 128188675-(2-Phthalimidoethylamino)-1,3,6-trimethylpyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

24.7 g. 5-Amino-1,3,6-trimethylpyrimidine-2,4(1H,3H)-dione, 44.5 g. N-(2-bromoethyl)-phthalimide and 30.2 g. potassium carbonate are stirred in 450 ml. acetonitrile for 4 days in an autoclave at 110° to 130° C. The inorganic salts are filtered off with suction and the filtrate is evaporated. The residue is purified over silica gel using ethyl acetate as elution agent. There are obtained 13.7 g. (27% of theory) of the desired product in the form of colorless crystals; m.p. 178°-180° C.

Workup

  1. filtrationThe inorganic salts are filtered off with suction
  2. customthe filtrate is evaporated
  3. customThe residue is purified over silica gel
  4. washas elution agent
  5. customThere are obtained 13.7 g

Sources & evidence

ORD record
ord-0bea65807b524bdd940f520245c88d7a
Source dataset
uspto-grants-1986_08
Patent number
US04608383

Reaction notes

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