Hydrochloric Acid → 7-chloro-3-(2,6-dichlorophenyl)-4-imino-1-methyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 1891041Notes

Reaction equation

HRID 1891041 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].CI.[Cl:9][C:10]1[N:15]=[C:14]2[NH:16][C:17](=O)[N:18]([C:21]3[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:28])[C:19](=[NH:20])[C:13]2=[CH:12][N:11]=1.Cl>C(OCC)(=O)C.CN(C)C=O>[Cl:9][C:10]1[N:15]=[C:14]2[N:16]([CH3:17])[C:1](=[O:4])[N:18]([C:21]3[C:22]([Cl:28])=[CH:23][CH:24]=[CH:25][C:26]=3[Cl:27])[C:19](=[NH:20])[C:13]2=[CH:12][N:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178507161HCID 178507161, compound

Product 1

HCID 582897897-chloro-3-(2,6-dichlorophenyl)-4-imino-1-methyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-oneYield 67.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

484 mg of potassium carbonate and 456 mg of methyl iodide were added to a 5-mL N,N-dimethylformamide solution containing 1.00 g of the 7-chloro-3-(2,6-dichlorophenyl)-4-imino-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one obtained in Production Example 1, and the mixture was stirred for 1 hour at room temperature. The reaction mixture was added to ethyl acetate and a 0.5 N hydrochloric acid aqueous solution with stirring to separate the organic layer. After washing with saturated saline, the solution was dried with anhydrous sodium sulfate, and the solvent was distilled away. The crude product was solidified using chloroform-methanol-hexane, and 700 mg of a yellow solid was obtained as a subject compound.

Workup

  1. customobtained in Production Example 1
  2. customto separate the organic layer
  3. washAfter washing with saturated saline
  4. dry with materialthe solution was dried with anhydrous sodium sulfate
  5. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-10bd4cddca3e42328afeb4543c400b41
Source dataset
uspto-grants-2013_08
Patent number
US08507505B2

Reaction notes

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