Triethylamine → HCID 57877719, compound

HRID 1091395Notes

Reaction equation

HRID 1091395 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[O:14][CH2:13][CH2:12][NH:11][CH2:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[C:23]1[N:28]([CH3:29])[C:27](=[O:30])[CH:26]=[C:25]([C:31]2[CH:36]=[CH:35][N:34]=[C:33]([Cl:37])[C:32]=2[Cl:38])[N:24]=1>O1CCCC1>[Cl:37][C:33]1[C:32]([Cl:38])=[C:31]([C:25]2[N:24]=[C:23]([N:11]3[CH2:12][CH2:13][O:14][C@@H:9]([C:6]4[CH:5]=[CH:4][C:3]([F:2])=[CH:8][CH:7]=4)[CH2:10]3)[N:28]([CH3:29])[C:27](=[O:30])[CH:26]=2)[CH:36]=[CH:35][N:34]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 57364135HCID 57364135, compoundHCID 86233545HCID 86233545, compound

Product 1

HCID 57877719HCID 57877719, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S)-2-(4-fluorophenyl)morpholine hydrochloride (0.8 g, 3.68 mmol) and triethylamine (2.1 g, 20.8 mmol) in tetrahydrofuran (20 ml) was added 2-chloro-6-(2,3-dichloropyridin-4-yl)-3-methyl-3H-pyrimidin-4-one (2.0 g, 6.88 mmol) portionwise and the mixture was stirred for 12 hours. The resulting suspension was partitioned between chloroform and 1N sodium hydroxide and the aqueous layer was extracted with chloroform. The combined organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography eluting 5-10% methanol in chloroform to furnish 6-(2,3-dichloropyridin-4-yl)-2-((2S)-2-(4-fluorophenyl)morpholin-4-yl)-3-methyl-3H-pyrimidin-4-one (1.1 g, 2.53 mmol, 69%) as white crystals.

Workup

  1. customThe resulting suspension was partitioned between chloroform and 1N sodium hydroxide
  2. extractionthe aqueous layer was extracted with chloroform
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting 5-10% methanol in chloroform

Sources & evidence

ORD record
ord-5bea24957c604a109bb51a033516a986
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

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