Hydrazine hydrate (1:1) → HCID 22125191, compound

HRID 1858266Notes

Reaction equation

HRID 1858266 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][N:35]4C(=O)C5=CC=CC=C5C4=O)[CH:28]=3)[C:15](=[O:26])[N:16]([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[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.O.NN>CO>[NH2:35][CH2:34][CH2:33][C:29]1[CH:28]=[C:27]([N:14]2[C:12]3=[N:13][C:8]([NH:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[N:9][CH:10]=[C:11]3[CH2:17][N:16]([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=3[Cl:25])[C:15]2=[O:26])[CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22125136HCID 22125136, compound

Product 1

HCID 22125191HCID 22125191, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 90 mg (0.14 mmol) of 7-anilino-3-(2,5-dichlorophenyl)-3,4-dihydro-1-[3-(2-phthalimidoethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one and 0.07 ml of hydrazine hydrate in 15 ml of methanol was stirred at room temperature under an atmosphere of nitrogen for 18 hours. The reaction was evaporated and the residue purified by flash column chromatography on silica gel, eluting with dichloromethane/methanol/acetic acid/water (240:24:3:2). Product containing fractions were combined and evaporated and the residue re-evaporated with toluene. The residue was then dissolved in 20 ml of dichloromethane, washed with 20 ml of saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and evaporated to give 37 mg (52%) of 1-[3-(2-aminoethyl)phenyl]-7-anilino-3-(2,5-dichlorophenyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 120-123° C. [Mass spectrum (ESI) MH+ =505].

Workup

  1. customThe reaction was evaporated
  2. customthe residue purified by flash column chromatography on silica gel
  3. washeluting with dichloromethane/methanol/acetic acid/water (240:24:3:2)
  4. additionProduct containing fractions
  5. customevaporated
  6. customthe residue re-evaporated with toluene
  7. dissolutionThe residue was then dissolved in 20 ml of dichloromethane
  8. washwashed with 20 ml of saturated aqueous sodium bicarbonate
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-edb1faf0b89b417b951cecfc72cd0b34
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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