Hydrochloric Acid → 6-(3-(2-(4-fluorophenyl)ethylamino)pyridin-4-yl)-3-methyl-2-(morpholin-4-yl)-3H-pyrimidin-4-one hydrochloride

HRID 1091400Notes

Reaction equation

HRID 1091400 reaction equation
F[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[N:13]=[C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:11]([CH3:20])[C:10](=[O:21])[CH:9]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][NH2:31])=[CH:25][CH:24]=1.[ClH:32]>CO>[ClH:32].[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][NH:31][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]([CH3:20])[C:10](=[O:21])[CH:9]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4653p-FluorophenethylamineHCID 578777672-(morpholin-4-yl)-3-methyl-6-(3-fluoropyridin-4-yl)-3H-pyrimidin-4-one

Product 1

HCID 665949026-(3-(2-(4-fluorophenyl)ethylamino)pyridin-4-yl)-3-methyl-2-(morpholin-4-yl)-3H-pyrimidin-4-one hydrochlorideYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 6-(3-fluoropyridin-4-yl)-3-methyl-2-(morpholin-4-yl)-3H-pyrimidin-4-one (0.60 g, 2.07 mmol), and 2-(4-fluorophenyl)ethylamine (2.9 g, 20.8 mmol) was heated at 120° C. for 8 hours. The resulting suspension was partitioned between chloroform and brine 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 a colorless oil. The methanol (10 ml) solution of resulting oil was treated with 4N hydrochloric acid (5 ml). The residue obtained by evaporation was washed by ethyl acetate to furnish 6-(3-(2-(4-fluorophenyl)ethylamino)pyridin-4-yl)-3-methyl-2-(morpholin-4-yl)-3H-pyrimidin-4-one hydrochloride (0.45 g, 1.01 mmol, 49%) as white crystals.

Workup

  1. customThe resulting suspension was partitioned between chloroform and brine
  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
  8. customto furnish a colorless oil
  9. customThe residue obtained by evaporation
  10. washwas washed by ethyl acetate

Sources & evidence

ORD record
ord-6bd69692ef20400b82ab89b81e3e1b5d
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

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