Triethylamine → 2-((2RS)-2-benzyl-pyrrolidin-1-yl)-6-(3-fluoro-pyridin-4-yl)-3-methyl-3H-pyrimidin-4-one

HRID 1045702Notes

Reaction equation

HRID 1045702 reaction equation
Cl[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[F:16])[N:3]=1.[CH2:17]([CH:24]1[CH2:28][CH2:27][CH2:26][NH:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>O1CCCC1>[CH2:17]([CH:24]1[CH2:28][CH2:27][CH2:26][N:25]1[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][C:11]=2[F:16])[N:3]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3395562-BenzylpyrrolidineHCID 595768122-Chloro-3-methyl-6-(3-fluoropyridin-4-yl)-3H-pyrimidin-4-one

Product 1

HCID 578699612-((2RS)-2-benzyl-pyrrolidin-1-yl)-6-(3-fluoro-pyridin-4-yl)-3-methyl-3H-pyrimidin-4-oneYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-chloro-6-(3-fluoropyridin-4-yl)-3-methyl-3H-pyrimidin-4-one (0.24 g, 1.0 mmol), (2RS)-2-benzyl-pyrrolidine (0.20 g, 1.2 mmol) and triethylamine (0.3 g, 3.0 mmol) in tetrahydrofuran (4 ml) was stirred for 5 hours at 40° C. The solution was partitioned between water and ethyl acetate, and the organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; chloroform/ethyl acetate=3/2) to afford 2-((2RS)-2-benzyl-pyrrolidin-1-yl)-6-(3-fluoro-pyridin-4-yl)-3-methyl-3H-pyrimidin-4-one (0.29 g, 80%).

Workup

  1. customThe solution was partitioned between water and ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; chloroform/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-1a9a6d8f250b4e258f6d6bcba3c1f301
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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