HCID 135838358, compound → HCID 135838359, compound

HRID 255730Notes

Reaction equation

HRID 255730 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([N:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)=[O:15])=[C:12]([CH3:23])[N:11]=[C:10]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:9]=2)=[CH:4][C:3]=1[N+:30]([O-])=O>[Pd].CO>[NH2:30][C:3]1[CH:4]=[C:5]([C:8]2[C:13]([C:14]([N:16]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]3)=[O:15])=[C:12]([CH3:23])[N:11]=[C:10]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:9]=2)[CH:6]=[CH:7][C:2]=1[OH:1]

Participants

4

Reactant 1

HCID 135838358HCID 135838358, compound

Product 1

HCID 135838359HCID 135838359, compoundYield 26.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(4-hydroxy-3-nitrophenyl)-6-methyl-5-(4-methylpiperazin-1-ylcarbonyl)-2-phenylpyrimidine (0.8 g) and 10% Palladium on carbon (0.2 g) in methanol (30 ml) was hydrogenated at room temperature under atmospheric pressure. After removal of the catalyst by filtration, the filtrate was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel (100 g) and eluted with a mixture of chloroform and methanol (30:1). The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was recrystallized from diethyl ether to give 4-(3-amino-4-hydroxyphenyl)-6-methyl-5-(4-methylpiperazin-1-ylcarbonyl)-2-phenylpyrimidine (0.2 g).

Workup

  1. customwas hydrogenated at room temperature under atmospheric pressure
  2. customAfter removal of the catalyst
  3. filtrationby filtration
  4. customthe filtrate was evaporated under reduced pressure
  5. washeluted with a mixture of chloroform and methanol (30:1)
  6. additionThe fractions containing the object compound
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-e612052e198d48939b8796bb0a6bccb6
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

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