N-Ethylaniline → 4-(4,6-Di(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrimidin-2-yl)aniline

HRID 75419

Reaction equation

HRID 75419 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]([N:24]3[CH2:30][CH:29]4[O:31][CH:26]([CH2:27][CH2:28]4)[CH2:25]3)[N:11]=2)=[CH:6][CH:5]=1)([O-])=O.C(NC1C=CC=CC=1)C>C(O)C.[Pd]>[CH:29]12[O:31][CH:26]([CH2:27][CH2:28]1)[CH2:25][N:24]([C:12]1[CH:13]=[C:14]([N:16]3[CH2:22][CH:21]4[O:23][CH:18]([CH2:19][CH2:20]4)[CH2:17]3)[N:15]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=3)[N:11]=1)[CH2:30]2

Participants

5

Reactant 2

HCID 7670N-EthylanilineHCID 667500373,3'-(2-(4-Nitrophenyl)pyrimidine-4,6-diyl)bis(8-oxa-3-azabicyclo[3.2.1]octane)

Product 1

HCID 667501314-(4,6-Di(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrimidin-2-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 250 mL round-bottomed flask was placed 3,3′-(2-(4-nitrophenyl)pyrimidine-4,6-diyl)bis(8-oxa-3-azabicyclo[3.2.1]octane) (20, 65 mg, 0.15 mmol) in ethanol (3 ml). A catalytic amount of Pd on charcoal (wet) was added and the mixture was stirred under a hydrogen atmosphere for 16 hours. The mixture was filtered over Celite™, rinsed with dichloromethane and concentrated to give a quantitative yield of the title compound along with an impurity (the N-ethyl aniline product). The crude mixture was reacted in the next step.

Workup

  1. customIn a 250 mL round-bottomed flask was placed
  2. filtrationThe mixture was filtered over Celite™
  3. washrinsed with dichloromethane
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d30633efe792499989256bbf86cc89e2
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Linked notes

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