HCID 20654285, compound → (7RS,9aSR)-7-Phenoxymethyl-2-(pyrimidin-4-yl)-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine

HRID 1352688Notes

Reaction equation

HRID 1352688 reaction equation
[O:1]([CH2:8][CH:9]1[CH2:25][N:13]2[CH2:14][CH2:15][N:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20](Cl)[N:19]=3)[CH2:17][CH:12]2[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>Cl.C(O)C.[Pd]>[O:1]([CH2:8][CH:9]1[CH2:25][N:13]2[CH2:14][CH2:15][N:16]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][N:19]=3)[CH2:17][CH:12]2[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 20654285HCID 20654285, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20654281(7RS,9aSR)-7-Phenoxymethyl-2-(pyrimidin-4-yl)-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazineYield 20.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.110 g (0.307 mmol) of (7RS,9aSR)-7-phenoxymethyl-2-(2-chloropyrimidin4-yl)-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine (Example 29), 20 mg of 10% Pd/C, and several drops of conc. hydrochloric acid in 30 mL of ethanol were shaken under 50 psi of hydrogen gas at room temperature for 6 h. The mixture was filtered through Celite and the filtrate was evaportated. The residue was basified with conc. ammonium hydroxide, extracted with chloroform, dried (magnesium sulfate), filtered and evaporated. Purification by flash silica gel chromatography with a solvent gradient from 100% chloroform to 95:5 chloroform:methanol gave 0.020 g (20%) of the title compound. mp (.HCl) >265° C. (dec). HRMS calc for C19H24N4O: 324.1945, found: 324.1970.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. extractionextracted with chloroform
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash silica gel chromatography with a solvent gradient from 100% chloroform to 95:5 chloroform

Sources & evidence

ORD record
ord-5e181a8716194a1991c813be5f63ea62
Source dataset
uspto-grants-2007_05
Patent number
US07220753B2

Reaction notes

Loading…