Triethylamine → HCID 86634396, compound

HRID 1045656Notes

Reaction equation

HRID 1045656 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.[O:17]1[CH2:22][CH2:21][NH:20][C@@H:19]2[CH2:23][CH2:24][C:25]3[C:30]([C@@H:18]12)=[CH:29][CH:28]=[CH:27][CH:26]=3.C(N(CC)CC)C>O1CCCC1>[O:17]1[CH2:22][CH2:21][N:20]([C:2]2[N:7]([CH3:8])[C:6](=[O:9])[CH:5]=[C:4]([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][N:11]=3)[N:3]=2)[C@@H:19]2[CH2:23][CH2:24][C:25]3[C:30]([C@@H:18]12)=[CH:29][CH:28]=[CH:27][CH:26]=3

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 179544602-Chloro-3-methyl-6-(pyrimidin-4-YL)pyrimidin-4-oneHCID 22824854HCID 22824854, compound

Product 1

HCID 86634396HCID 86634396, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-chloro-3-methyl-6-(pyrimidin-4-yl)-3H-pyrimidin-4-one (0.25 g, 1.12 mmol), (4aRS,10bRS)-trans-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazine hydrochloride (0.3 g, 1.33 mmol) and triethylamine (0.4 g, 3.95 mmol) in tetrahydrofuran (15 ml) was stirred for 48 hours at 100° C. The mixture 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 give 2-((4aRS,10bRS)-trans-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazin-4-yl)-3-methyl-6-(pyrimidin-4-yl)-3H-pyrimidin-4-one (72 mg, 0.19 mmol, 16%) as pale white crystals.

Workup

  1. customThe mixture 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-c721683259244ba5819af14fa8529fa1
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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