9-(6-Chloro-2-(4-nitrophenyl)pyrimidin-4-yl)-3,7-dioxa-9-azabicyclo[3.3.1]nonane → HCID 66750356, compound

HRID 75454Notes

Reaction equation

HRID 75454 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[N:5]=[C:4]([N:17]2[CH:22]3[CH2:23][O:24][CH2:25][CH:18]2[CH2:19][O:20][CH2:21]3)[CH:3]=1>C(N)(C)C>[CH:22]12[N:17]([C:4]3[N:5]=[C:6]([C:8]4[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=4)[N:7]=[C:2]([NH:14][CH:11]([CH3:12])[CH3:10])[CH:3]=3)[CH:18]([CH2:25][O:24][CH2:23]1)[CH2:19][O:20][CH2:21]2

Participants

3

Reactant 1

HCID 866659039-(6-Chloro-2-(4-nitrophenyl)pyrimidin-4-yl)-3,7-dioxa-9-azabicyclo[3.3.1]nonane

Product 1

HCID 66750356HCID 66750356, compoundYield 198.6%

Reagents, catalysts & solvents 1

HCID 6363IsopropylamineSolvent

Conditions

Temperature
145 °C

Procedure

In a 2-5 mL microwave vial was placed 9-(6-chloro-2-(4-nitrophenyl)pyrimidin-4-yl)-3,7-dioxa-9-azabicyclo[3.3.1]nonane (130 mg, 0.358 mmol) in isopropylamine (5 mL) to give a yellow suspension. The reaction was heated under microwave irradiation at 145° C. for 60 min. The mixture was concentrated. The residue was dissolved in dichloromethane and washed with saturated NaHCO3. The organic phase was dried (MgSO4), filtered and concentrated to give 137 mg (99%) of a yellow foam. HRMS: 386.1824 [M+H]+. For [M+H]+ mass error=0.1 mDa or 0.21 ppm.

Workup

  1. customto give a yellow suspension
  2. concentrationThe mixture was concentrated
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with saturated NaHCO3
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3fca1d644e9a48ad966b12bef025fdb2
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Reaction notes

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