4-Ethoxyaniline → HCID 22125149, compound

HRID 1858294Notes

Reaction equation

HRID 1858294 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]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:10]1=[O:29].[CH2:30]([O:32][C:33]1[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=1)[CH3:31]>>[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:37][C:36]3[CH:38]=[CH:39][C:33]([O:32][CH2:30][CH3:31])=[CH:34][CH:35]=3)=[N:15][CH:16]=2)[N:11]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:10]1=[O:29]

Participants

3

Reactant 2

HCID 90764-EthoxyanilineHCID 22125142HCID 22125142, compound

Product 1

HCID 22125149HCID 22125149, compoundYield 71.1%

Conditions

Temperature
90 °C

Procedure

A mixture of 158 mg (0.35 mmol) of 3-(2,6-dichlorophenyl)-7-methanesulfonyl-3,4-dihydro-1-phenylpyrimido[4,5-d]pyrimidin-2(1H)-one (prepared in Example 7) and 250 μl (1.9 mmol) of 4-ethoxyaniline were heated at 90° C. for 2 hours. The reaction mixture was partitioned between dichloromethane (10 ml) and 2M hydrochloric acid (10 ml) and the dichloromethane layer separated, washed with saturated aqueous sodium bicarbonate (10 ml), dried over magnesium sulfate, filtered and evaporated. The crude material was purified by flash chromatography on silica gel, eluting with 1:1 ethyl acetate/hexane. Product containing fractions were combined and evaporated to give 126 mg (71%) of 3-(2,6-dichlorophenyl)-7-(4-ethoxyanilino)-3,4-dihydro-1-phenylpyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 224-226° C. [Mass spectrum (ESI) MH+ =506].

Workup

  1. customThe reaction mixture was partitioned between dichloromethane (10 ml) and 2M hydrochloric acid (10 ml)
  2. customthe dichloromethane layer separated
  3. washwashed with saturated aqueous sodium bicarbonate (10 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude material was purified by flash chromatography on silica gel
  8. washeluting with 1:1 ethyl acetate/hexane
  9. additionProduct containing fractions
  10. customevaporated

Sources & evidence

ORD record
ord-aec0d07172fc4b5698c86c02da6faba0
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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