Triethylamine → 3-methyl-2-((3R)-3-methylmorpholin-4-yl)-6-(pyrimidin-4-yl)-3H-pyrimidin-4-one

HRID 1045669Notes

Reaction equation

HRID 1045669 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][N:11]=2)[N:3]=1.Cl.[CH3:17][C@@H:18]1[CH2:23][O:22][CH2:21][CH2:20][NH:19]1.C(N(CC)CC)C>O1CCCC1>[CH3:8][N:7]1[C:6](=[O:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][N:11]=2)[N:3]=[C:2]1[N:19]1[CH2:20][CH2:21][O:22][CH2:23][C@H:18]1[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 179544602-Chloro-3-methyl-6-(pyrimidin-4-YL)pyrimidin-4-oneHCID 57356922(3R)-3-Methylmorpholine hydrochloride

Product 1

HCID 578700273-methyl-2-((3R)-3-methylmorpholin-4-yl)-6-(pyrimidin-4-yl)-3H-pyrimidin-4-oneYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-chloro-3-methyl-6-(pyrimidin-4-yl)-3H-pyrimidin-4-one (0.32 g, 1.44 mmol), (3R)-3-methylmorpholine hydrochloride (0.4 g, 2.9 mmol) and triethylamine (0.9 g, 8.9 mmol) in tetrahydrofuran (20 ml) was stirred for 10 hours at 100° C. The solution was partitioned between water and chloroform, and the organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform) to afford 3-methyl-2-((3R)-3-methylmorpholin-4-yl)-6-(pyrimidin-4-yl)-3H-pyrimidin-4-one (0.31 g, 1.08 mmol, 75%) as white crystals.

Workup

  1. customThe solution was partitioned between water and chloroform
  2. washthe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform)

Sources & evidence

ORD record
ord-9bc5ff64cdad4dbbb657d8a685260f55
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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