HCID 86665886, compound → 3-[2,6-Bis-(4-aminophenyl)-pyrimidin-4-yl]-8-oxa-3-aza-bicyclo[3.2.1]octane

HRID 75422Notes

Reaction equation

HRID 75422 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]([N:16]3[CH2:22][CH:21]4[O:23][CH:18]([CH2:19][CH2:20]4)[CH2:17]3)[CH:13]=[C:12]([C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=3)[N:11]=2)=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]([N:16]3[CH2:17][CH:18]4[O:23][CH:21]([CH2:20][CH2:19]4)[CH2:22]3)[CH:13]=[C:12]([C:24]3[CH:25]=[CH:26][C:27]([NH2:30])=[CH:28][CH:29]=3)[N:11]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 86665886HCID 86665886, compound

Product 1

HCID 667503693-[2,6-Bis-(4-aminophenyl)-pyrimidin-4-yl]-8-oxa-3-aza-bicyclo[3.2.1]octane

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 500 mL round-bottomed flask was placed 3-[2,6-bis-(4-nitro-phenyl)-pyrimidin-4-yl]-8-oxa-3-aza-bicyclo[3.2.1]octane (15) in ethanol (100 ml). A catalytic amount of Pd on charcoal (wet) was added and the mixture was stirred under a hydrogen atmosphere for 40 h. The mixture was filtered over Celite™, rinsed with MeOH, and concentrated. The crude product was added to a silica gel column and eluted with ethyl acetate in hexanes (40-100%) to give 295 mg of the title compound (0.79 mmol).

Workup

  1. customIn a 500 mL round-bottomed flask was placed
  2. filtrationThe mixture was filtered over Celite™
  3. washrinsed with MeOH
  4. concentrationconcentrated
  5. additionThe crude product was added to a silica gel column
  6. washeluted with ethyl acetate in hexanes (40-100%)

Sources & evidence

ORD record
ord-c132c91f695b4d158b677c1e689497f3
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Reaction notes

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