Isopropyl-[2-(4-nitro-phenyl)-6-(8-oxa-3-aza-bicyclo[3.2.1]oct-3-yl)-pyrimidin-4-yl]-amine → HCID 66750677, compound

HRID 75416Notes

Reaction equation

HRID 75416 reaction equation
[CH:1]([NH:4][C:5]1[CH:10]=[C:9]([N:11]2[CH2:17][CH:16]3[O:18][CH:13]([CH2:14][CH2:15]3)[CH2:12]2)[N:8]=[C:7]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)[N:6]=1)([CH3:3])[CH3:2]>CC(O)C.ClCCl.[Pd]>[NH2:25][C:22]1[CH:21]=[CH:20][C:19]([C:7]2[N:6]=[C:5]([NH:4][CH:1]([CH3:3])[CH3:2])[CH:10]=[C:9]([N:11]3[CH2:12][CH:13]4[O:18][CH:16]([CH2:15][CH2:14]4)[CH2:17]3)[N:8]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 1

HCID 66750217Isopropyl-[2-(4-nitro-phenyl)-6-(8-oxa-3-aza-bicyclo[3.2.1]oct-3-yl)-pyrimidin-4-yl]-amine

Product 1

HCID 66750677HCID 66750677, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

In a 250 mL round-bottomed flask was placed 6-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-N-isopropyl-2-(4-nitrophenyl)pyrimidin-4-amine (17, 74 mg, 0.200 mmol) in 2-propanol (7 mL) and dichloromethane (7 mL) to give a yellow solution. A catalytic amount of Pd on charcoal (wet) was added and the mixture was stirred under a hydrogen atmosphere for 1 hour. The mixture was filtered over Celite™, rinsed with dichloromethane and concentrated to give the title compound in quantitative yield.

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-49f2778e3a2046b8b64f3bca8bce6fde
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Reaction notes

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