Hydrochloric Acid → HCID 53628937, compound

HRID 1784665Notes

Reaction equation

HRID 1784665 reaction equation
Cl.N1([C:7]2[CH:12]=[CH:11][C:10]([CH:13]3[CH2:18][CH2:17][CH2:16][N:15]([C:19](OC(C)(C)C)=O)[CH2:14]3)=[C:9](C)[CH:8]=2)CCCC1.[CH2:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])C.Cl[C:35]1[N:40](C)[C:39](=[O:42])[CH:38]=[C:37]([C:43]2[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=2)[N:36]=1.[C:49]([OH:56])(=[O:55])/[CH:50]=[CH:51]/[C:52]([OH:54])=[O:53]>C(OCC)(=O)C.CC(C)=O.O1CCCC1>[C:49]([OH:56])(=[O:55])/[CH:50]=[CH:51]/[C:52]([OH:54])=[O:53].[CH3:35][N:40]1[C:39](=[O:42])[CH:38]=[C:37]([C:43]2[CH:44]=[CH:45][N:46]=[CH:47][CH:48]=2)[N:36]=[C:19]1[N:15]1[CH2:16][CH2:17][CH2:18][CH:13]([C:10]2[CH:9]=[CH:8][C:7]([CH2:27][N:29]3[CH2:32][CH2:33][CH2:31][CH2:30]3)=[CH:12][CH:11]=2)[CH2:14]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 444972Fumaric AcidHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-HCID 53628939HCID 53628939, compound

Product 1

HCID 53628937HCID 53628937, compoundYield 84.4%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4N Hydrogen chloride in ethyl acetate was added to 3-(4-(1-pyrrolidinyl)-methylphenyl)-1-(tert-butoxycarbonyl)piperidine (0.26 g, 0.75 mmol) and stirred overnight. After filtration and dryness, triethylamine (0.5 ml, 3.6 mmol), 2-chloro-3-methyl-6-(4-pyridyl)-pyrimidin-4-one (0.14 g, 0.63 mmol) and tetrahydrofuran were added and stirred at 70° C. Organic solvents were removed under reduced pressure after addition of water and extracted with ethyl acetate, washed with water and brine and dried over sodium sulfate. Removal of the solvent under reduced pressure and the residue was dissolved into ethyl acetate. A solution of fumaric acid (0.095 g, 0.82 mmol) in acetone was added and the resulting precipitate was filtered and dried to give the title compound (0.29 g, 76%).

Workup

  1. additionwere added
  2. stirringstirred at 70° C
  3. customOrganic solvents were removed under reduced pressure
  4. additionafter addition of water
  5. extractionextracted with ethyl acetate
  6. washwashed with water and brine
  7. dry with materialdried over sodium sulfate
  8. customRemoval of the solvent under reduced pressure
  9. dissolutionthe residue was dissolved into ethyl acetate
  10. filtrationthe resulting precipitate was filtered
  11. customdried

Sources & evidence

ORD record
ord-d3c0b0bfe2f9418e80b26d8f079d9bbf
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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