2-(4-Aminophenyl)ethylamine → HCID 22125155, compound

HRID 1858217Notes

Reaction equation

HRID 1858217 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].[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][NH2:34])=[CH:28][CH:27]=1>>[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][NH:34][C:14]2[N:13]=[C:12]3[N:11]([CH3:23])[C:10](=[O:24])[N:9]([C:3]4[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=4[Cl:8])[CH2:18][C:17]3=[CH:16][N:15]=2)=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 728952-(4-Aminophenyl)ethylamineHCID 184254443-(2,6-dichlorophenyl)-7-methanesulfonyl-1-methyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

Product 1

HCID 22125155HCID 22125155, compoundYield 3%

Conditions

Temperature
70 °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 140 mg (1 mmol) of 2-(4-aminophenyl)ethylamine was heated at 70° C. for 20 minutes. The product was purified by flash column chromatography using 5% methanol in dichloromethane for the elution. Product-containing fractions were combined and evaporated. The residue was recrystallized from ethyl acetate and 3 mg (3%) of 7-[2-(4-aminophenyl)ethylamino]-3-(2,6-dichlorophenyl)-3,4-dihydro-1-methylpyrimido[4,5-d]pyrimidin-2(1H)-one were isolated as a yellow solid of melting point 174-175° C.

Workup

  1. customThe product was purified by flash column chromatography
  2. washfor the elution
  3. customevaporated
  4. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-438141c0e0c44016bb81342fb9b52040
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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