Triethylamine → HCID 25004257, compound

HRID 1045688Notes

Reaction equation

HRID 1045688 reaction equation
Cl.Cl.[CH2:3]([NH:10][C@@H:11]1[CH2:15][CH2:14][NH:13][CH2:12]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:17]1[N:22]([CH3:23])[C:21](=[O:24])[CH:20]=[C:19]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[N:18]=1.C(N(CC)CC)C>O1CCCC1>[CH2:3]([NH:10][C@@H:11]1[CH2:15][CH2:14][N:13]([C:17]2[N:22]([CH3:23])[C:21](=[O:24])[CH:20]=[C:19]([C:25]3[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=3)[N:18]=2)[CH2:12]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-HCID 66771352HCID 66771352, compound

Product 1

HCID 25004257HCID 25004257, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-benzylpyrrolidin-3-yl-amine dihydrochloride (3.0 g, 12 mmol), 2-chloro-3-methyl-6-(pyridin-4-yl)-3H-pyrimidin-4-one (2.6 g, 12 mmol), and triethylamine (6 g, 60 mmol) in tetrahydrofuran (40 ml) was stirred for 12 hours at 95° C. The solvent was evaporated off under reduced pressure and the residue was partitioned between water and dichloromethane. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; ethyl acetate) to afford 2-((R)-3-benzylaminopyrrolidin-1-yl)-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one (3.2 g, 75%) as pale yellow oil.

Workup

  1. customThe solvent was evaporated off under reduced pressure
  2. customthe residue was partitioned between water and dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent; ethyl acetate)

Sources & evidence

ORD record
ord-06baec8081fd4ef19030d930792b15c0
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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