8,8'-(2-(4-Nitrophenyl)pyrimidine-4,6-diyl)bis(3-oxa-8-azabicyclo[3.2.1]octane) → HCID 66750288, compound

HRID 75433Notes

Reaction equation

HRID 75433 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[C:14]([N:16]3[CH:21]4[CH2:22][CH2:23][CH:17]3[CH2:18][O:19][CH2:20]4)[CH:13]=[C:12]([N:24]3[CH:29]4[CH2:30][CH2:31][CH:25]3[CH2:26][O:27][CH2:28]4)[N:11]=2)=[CH:6][CH:5]=1)([O-])=O>CC(O)C.ClCCl.[Pd]>[CH:25]12[N:24]([C:12]3[CH:13]=[C:14]([N:16]4[CH:21]5[CH2:22][CH2:23][CH:17]4[CH2:18][O:19][CH2:20]5)[N:15]=[C:10]([C:7]4[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=4)[N:11]=3)[CH:29]([CH2:30][CH2:31]1)[CH2:28][O:27][CH2:26]2

Participants

5

Reactant 1

HCID 667501958,8'-(2-(4-Nitrophenyl)pyrimidine-4,6-diyl)bis(3-oxa-8-azabicyclo[3.2.1]octane)

Product 1

HCID 66750288HCID 66750288, compoundYield 86.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

In a 250 mL round-bottomed flask was placed 8,8′-(2-(4-nitrophenyl)pyrimidine-4,6-diyl)bis(3-oxa-8-azabicyclo[3.2.1]octane) (37, 246 mg, 0.581 mmol) in 2-propanol (3 mL) and dichloromethane (3 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 4 hours. The mixture was filtered over Celite™, rinsed with dichloromethane and concentrated. The crude product was added to a silica gel column and was eluted with ethyl acetate in hexanes (40-60%). Collected fractions were concentrated to give the title compound (197 mg, 0.5 mmol, 86%) as a light yellow solid. For [M+H]+ mass error=0.2 mDa or 0.46 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
  5. additionThe crude product was added to a silica gel column
  6. washwas eluted with ethyl acetate in hexanes (40-60%)
  7. concentrationCollected fractions were concentrated

Sources & evidence

ORD record
ord-7107282d13384135a69bdf90d6aed282
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Reaction notes

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