HCID 66653485, compound → 4,6-Dimethoxy-2-(4-methoxypiperidin-1-yl)pyrimidin-5-amine

HRID 334326Notes

Reaction equation

HRID 334326 reaction equation
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-])=O)=[C:7]([O:12][CH3:13])[N:6]=[C:5]([N:14]2[CH2:19][CH2:18][CH:17]([O:20][CH3:21])[CH2:16][CH2:15]2)[N:4]=1>[Pd].CO>[CH3:13][O:12][C:7]1[C:8]([NH2:9])=[C:3]([O:2][CH3:1])[N:4]=[C:5]([N:14]2[CH2:19][CH2:18][CH:17]([O:20][CH3:21])[CH2:16][CH2:15]2)[N:6]=1

Participants

4

Reactant 1

HCID 66653485HCID 66653485, compound

Product 1

HCID 666531684,6-Dimethoxy-2-(4-methoxypiperidin-1-yl)pyrimidin-5-amineYield 108.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a 1 L Atlantis reactor, under nitrogen, was added 20% palladium on carbon (6.16 g, 5.79 mmol, 15% by weight), 4,6-dimethoxy-2-(4-methoxypiperidin-1-yl)-5-nitropyrimidine (41.1 g, 137.8 mmol) and methanol (390 mL). The reactor was sealed and purged with nitrogen (3×) and then hydrogen (3×). The mixture was hydrogenated at 50 psi (H2) for 3 h. After purging with nitrogen, the catalyst was removed by filtration, and the filter cake was rinsed with additional methanol (150 mL). The filtrate was concentrated to afford 40.25 g of 4,6-dimethoxy-2-(4-methoxypiperidin-1-yl)pyrimidin-5-amine as a viscous orange oil that was used without further purification. 1H NMR (400 MHz, CDCI3) δ 4.17-4.29 (m, 2H) 3.92 (s, 6H) 3.39 (s, 3H) 3.34-3.47 (m, 1H) 3.19 (ddd, J=13.0, 9.0, 3.0 Hz, 2H) 2.76 (br. s., 2H) 1.87-2.00 (m, 1H) 1.43-1.68 (m, 2H). LCMS m/z=269.1 (M+1).

Workup

  1. customThe reactor was sealed
  2. custompurged with nitrogen (3×)
  3. customAfter purging with nitrogen
  4. customthe catalyst was removed by filtration
  5. washthe filter cake was rinsed with additional methanol (150 mL)
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-fbe84db32e164c8ab908e6b6c899a10d
Source dataset
uspto-grants-2014_11
Patent number
US08883812B2

Reaction notes

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