6-(3-Oxa-8-azabicyclo[3.2.1]octan-8-yl)-N-isopropyl-2-(4-nitrophenyl)pyrimidin-4-amine → HCID 66750245, compound

HRID 75449Notes

Reaction equation

HRID 75449 reaction equation
[CH:1]12[N:8]([C:9]3[N:14]=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=4)[N:12]=[C:11]([NH:24][CH:25]([CH3:27])[CH3:26])[CH:10]=3)[CH:5]([CH2:6][CH2:7]1)[CH2:4][O:3][CH2:2]2>CC(O)C.ClCCl.[Pd]>[NH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:13]2[N:12]=[C:11]([NH:24][CH:25]([CH3:27])[CH3:26])[CH:10]=[C:9]([N:8]3[CH:5]4[CH2:6][CH2:7][CH:1]3[CH2:2][O:3][CH2:4]4)[N:14]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 1

HCID 667500696-(3-Oxa-8-azabicyclo[3.2.1]octan-8-yl)-N-isopropyl-2-(4-nitrophenyl)pyrimidin-4-amine

Product 1

HCID 66750245HCID 66750245, compoundYield 98.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

In a 250 mL round-bottomed flask was placed 6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-N-isopropyl-2-(4-nitrophenyl)pyrimidin-4-amine (60, 196 mg, 0.53 mmol) in 2-propanol (5 mL) and dichloromethane (5 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 16 hours. The mixture was filtered over Celite™, rinsed with dichloromethane and concentrated to give the title compound (176 mg, 0.52 mmol, 98%) as a yellow solid. HRMS: For [M+H]+ mass error=0.5 mDa or 1.46 ppm.

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-891cff70f1e7419cbb326a7fbae985a0
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Reaction notes

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