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

HRID 75421

Reaction equation

HRID 75421 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)[N:13]=[C:12]([N:24]3[CH2:30][CH:29]4[O:31][CH:26]([CH2:27][CH2:28]4)[CH2:25]3)[CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.C(NC1C=CC=CC=1)C>C(O)C.[Pd]>[CH:18]12[O:23][CH:21]([CH2:20][CH2:19]1)[CH2:22][N:16]([C:14]1[N:15]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=3)[CH:11]=[C:12]([N:24]3[CH2:25][CH:26]4[O:31][CH:29]([CH2:28][CH2:27]4)[CH2:30]3)[N:13]=1)[CH2:17]2

Participants

5

Reactant 2

HCID 7670N-EthylanilineHCID 667505783,3'-(6-(4-Nitrophenyl)pyrimidine-2,4-diyl)bis(8-oxa-3-azabicyclo[3.2.1]octane)

Product 1

HCID 667502704-(2,6-Di(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyrimidin-4-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 250 mL round-bottomed flask was placed 3,3′-(6-(4-nitrophenyl)pyrimidine-2,4-diyl)bis(8-oxa-3-azabicyclo[3.2.1]octane) (22, 89 mg, 0.21 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-82b5bb214ed549bba3fdeef104b3841f
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Linked notes

Loading…