Hydrazine hydrate (1:1) → HCID 22125108, compound

HRID 1858302Notes

Reaction equation

HRID 1858302 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]2[N:14]([C:27]3[CH:32]=[CH:31][C:30]([CH2:33][CH2:34][N:35]4C(=O)C5=CC=CC=C5C4=O)=[CH:29][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.O.NN>CO.ClCCl>[NH2:35][CH2:34][CH2:33][C:30]1[CH:31]=[CH:32][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]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[C:15]2=[O:26])=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22125051HCID 22125051, compound

Product 1

HCID 22125108HCID 22125108, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 195 mg (0.3 mmol) of 7-anilino-3-(2,4-dichlorophenyl)-3,4-dihydro-1-[4-(2-phthalimidoethyl)phenyl]-pyrimido[4,5-d]pyrimidin-2(1H)-one and 150 μl (3 mmol) of hydrazine hydrate in methanol/dichloromethane (3 ml:3 ml) was stirred at room temperature under an atmosphere of nitrogen overnight. The reaction mixture was evaporated and the residue purified by flash chromatography on silica gel eluting with dichloromethane/methanol/acetic acid/water (120:14:3:2). Product containing fractions were combined and evaporated and the residue re-evaporated with toluene. The residue was dissolved in 20 ml of dichloromethane, washed with saturated aqueous sodium bicarbonate (20 ml), dried over magnesium sulfate, filtered and evaporated to give 90 mg (67%) of 1-[4-(2-aminoethyl)phenyl]-7-anilino-3-(2,4-dichlorophenyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid of melting point 117-121° C. [Mass spectrum (ESI) MH+ =505].

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue purified by flash chromatography on silica gel eluting with dichloromethane/methanol/acetic acid/water (120:14:3:2)
  3. additionProduct containing fractions
  4. customevaporated
  5. customthe residue re-evaporated with toluene
  6. dissolutionThe residue was dissolved in 20 ml of dichloromethane
  7. washwashed with saturated aqueous sodium bicarbonate (20 ml)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-8bfadc09061942c8819701a4974ee625
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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