Phenethylamine → HCID 22125088, compound

HRID 1858211Notes

Reaction equation

HRID 1858211 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14](S(C)(=O)=O)=[N:15][CH:16]=2)[N:11]([CH3:23])[C:10]1=[O:24].[CH2:25]([NH2:33])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14]([NH:33][CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:15][CH:16]=2)[N:11]([CH3:23])[C:10]1=[O:24]

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 184254443-(2,6-dichlorophenyl)-7-methanesulfonyl-1-methyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

Product 1

HCID 22125088HCID 22125088, compoundYield 31.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 100 mg (0.26 mmol) of 3-(2,6-dichlorophenyl)-3,4-dihydro-7-methanesulfonyl-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one and 400 μl (3.4 mmol) of phenethylamine was heated at 180° C. for 4 hours and then cooled to room temperature. The mixture was dissolved in 10 ml of ethyl acetate and washed in sequence with 10 ml of 2M hydrochloric acid and 10 ml of saturated aqueous sodium bicarbonate solution. The ethyl acetate phase was separated, dried over magnesium sulfate, filtered and evaporated. The crude product was purified by flash column chromatography on silica gel using 5% methanol/dichloromethane for the elution. Product-containing fractions were combined and evaporated to give 35 mg of 3-(2,6-dichlorophenyl)-3,4-dihydro-1-methyl-7-(2-phenylethylamino)pyrimido[4,5-d]pyrimidin-2(1H)-one as a pale yellow solid of melting point 148-151° C.

Workup

  1. temperaturecooled to room temperature
  2. washwashed in sequence with 10 ml of 2M hydrochloric acid and 10 ml of saturated aqueous sodium bicarbonate solution
  3. customThe ethyl acetate phase was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash column chromatography on silica gel using 5% methanol/dichloromethane for the elution
  8. customevaporated

Sources & evidence

ORD record
ord-41dd489070a1493698d996933907c880
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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