HCID 13589479, compound → HCID 13589519, compound

HRID 2073614Notes

Reaction equation

HRID 2073614 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=2)[N:9]2[CH:20]=[CH:21][N:22]=[C:8]2[NH:7][C:6]=1[CH3:23])=[O:4]>[C].[Pd].C(O)(=O)C>[NH2:17][C:13]1[CH:12]=[C:11]([CH:10]2[N:9]3[CH:20]=[CH:21][N:22]=[C:8]3[NH:7][C:6]([CH3:23])=[C:5]2[C:3]([O:2][CH3:1])=[O:4])[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 13589479HCID 13589479, compound

Product 1

HCID 13589519HCID 13589519, compoundYield 60.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 20.0 g of 6-methoxycarbonyl-7-methyl-5-(3-nitrophenyl)-5,8-dihydroimidazo[1,2-a]pyrimidine, 200 ml of acetic acid and 3.0 g of 10 palladium-carbon is stirred at room temperature for 5 hours under hydrogen gas. After an insoluble material is filtered off, the filtrate is neutralized with sodium bicarbonate, and extracted with chloroform. The extract is dried and the solvent is distilled off under reduced pressure. The precipitated pale yellow crystals are collected by filtration and recrystallized from methanol to give 11.0 g of 5-(3-aminophenyl)-6-methoxycarbonyl-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine, melting at 224°-225° C.

Workup

  1. filtrationAfter an insoluble material is filtered off
  2. extractionextracted with chloroform
  3. customThe extract is dried
  4. distillationthe solvent is distilled off under reduced pressure
  5. filtrationThe precipitated pale yellow crystals are collected by filtration
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-30ee283ca9d04de38094e4cb6bc5d9a3
Source dataset
uspto-grants-1990_04
Patent number
US04918074

Reaction notes

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