Piperazine → HCID 22124974, compound

HRID 1858339Notes

Reaction equation

HRID 1858339 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]2[N:14]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][CH2:34]OS(C)(=O)=O)[CH:28]=3)[C:15](=[O:26])[N:16]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[CH2:17][C:11]2=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1>C(O)C>[NH:1]([C:8]1[N:13]=[C:12]2[N:14]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][CH2:34][N:40]4[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]4)[CH:28]=3)[C:15](=[O:26])[N:16]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[CH2:17][C:11]2=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 22125008HCID 22125008, compound

Product 1

HCID 22124974HCID 22124974, compoundYield 5.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 58 mg (0.1 mmol) of 7-anilino-3-(2,4-dichlorophenyl)-3,4-dihydro-1-[3-(2-methanesulfonyloxyethyl)phenyl]-pyrimido[4,5-d]pyrimidin-2(1H)-one (prepared in Example 74) and 100 mg of piperazine in 2 ml of ethanol was heated at 50° C. for 3 hours. The reaction mixture was evaporated and the crude material purified by flash chromatography on silica gel, eluting with dichloromethane/methanol/acetic acid/water (90:18:3:2). Product containing fractions were combined and evaporated. The residue was dissolved in 10 ml of dichloromethane, washed with saturated aqueous sodium bicarbonate (10 ml), dried over magnesium sulfate, filtered and evaporated to give 3 mg (5%) of 7-anilino-3-(2,4-dichlorophenyl)-3,4-dihydro-1-[3-[2-(1-piperazinyl)-ethyl]phenyl]-pyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 126° C. [Mass spectrum (ESI) MH+ =574].

Workup

  1. customThe reaction mixture was evaporated
  2. customthe crude material purified by flash chromatography on silica gel
  3. washeluting with dichloromethane/methanol/acetic acid/water (90:18:3:2)
  4. additionProduct containing fractions
  5. customevaporated
  6. dissolutionThe residue was dissolved in 10 ml of dichloromethane
  7. washwashed with saturated aqueous sodium bicarbonate (10 ml)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-8b3eed7b7f3441e79ba9fcf2fb2d7be3
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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