Triethylamine → HCID 57870005, compound

HRID 1045671Notes

Reaction equation

HRID 1045671 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.C([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])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:18]1[C@@H:19]2[CH2:20][CH2:10][CH2:4][CH2:5][C@H:6]2[O:9][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 179544602-Chloro-3-methyl-6-(pyrimidin-4-YL)pyrimidin-4-one

Product 1

HCID 57870005HCID 57870005, compoundYield 128.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-chloro-3-methyl-6-(pyrimidin-4-yl)-3H-pyrimidin-4-one (0.34 g, 1.53 mmol), (4aRS,8bRS)-trans-octahydrobenzo[1,4]oxazine hydrochloride (0.3 g, 1.69 mmol) and triethylamine (0.5 g, 4.94 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 1-methyl-2-((4aRS,8aRS)-trans-octahydro-benzo[1,4]oxazin-4-yl)-1H-[4,4′]bipyrimidinyl-6-one (0.32 g, 0.98 mmol, 64%) 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-6f2034ad2d994aeb9d1daa2dfae0d8f5
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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