Potassium Carbonate → 3-(2-Chloro-5-nitro-phenyl)-1-methyl-7-methylsulfanyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 1726913Notes

Reaction equation

HRID 1726913 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][CH2:12][C:13]1[C:14]([NH:21][CH3:22])=[N:15][C:16]([S:19][CH3:20])=[N:17][CH:18]=1.[C:23](=[O:26])([O-])[O-].[K+].[K+].C1N=CN(C(N2C=NC=C2)=O)C=1>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]1[CH2:12][C:13]2[C:14](=[N:15][C:16]([S:19][CH3:20])=[N:17][CH:18]=2)[N:21]([CH3:22])[C:23]1=[O:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 68700288{5-[(2-Chloro-5-nitro-phenylamino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl}-methyl-amine

Product 1

HCID 686978933-(2-Chloro-5-nitro-phenyl)-1-methyl-7-methylsulfanyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-oneYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

20.796 g {5-[(2-Chloro-5-nitro-phenylamino)-methyl]-2-methylsulfanyl-pyrimidin-4-yl}-methyl-amine were dissolved in 500 ml acetonitrile, 25.375 g potassium carbonate and 19.847 g N,N-carbonyldiimidazole (CDI) were added, and the solution was heated at 50° C. for 24 hrs. The solvent was dried over sodium sulfate, evaporated, and the residue was extracted with diethyl ether to give the title product in 96% yield.

Workup

  1. dry with materialThe solvent was dried over sodium sulfate
  2. customevaporated
  3. extractionthe residue was extracted with diethyl ether

Sources & evidence

ORD record
ord-d61fb5a9b9c64b76af8e83a9a25f797a
Source dataset
uspto-grants-2009_02
Patent number
US07494993B2

Reaction notes

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