Hydrochloric Acid → (S)-5'-fluoro-2-[2-(4-fluoro-phenyl)-morpholin-4-yl]-1-methyl-1H-[4,4']bipyrimidinyl-6-one

HRID 1429594Notes

Reaction equation

HRID 1429594 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.Cl[C:16]1[N:17]([CH3:30])[C:18](=[O:29])[CH:19]=[C:20]([C:22]2[C:27]([F:28])=[CH:26][N:25]=[CH:24][N:23]=2)[N:21]=1.C(N(CC)CC)C.Cl>O1CCCC1>[F:28][C:27]1[C:22]([C:20]2[N:21]=[C:16]([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:17]([CH3:30])[C:18](=[O:29])[CH:19]=2)=[N:23][CH:24]=[N:25][CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 57364135HCID 57364135, compoundHCID 679776592-chloro-5'-fluoro-1-methyl-1H-[4,4']bipyrimidinyl-6-one2×

Product 1

HCID 67977667(S)-5'-fluoro-2-[2-(4-fluoro-phenyl)-morpholin-4-yl]-1-methyl-1H-[4,4']bipyrimidinyl-6-oneYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (S)-2-(4-fluorophenyl)-morpholine hydrochloride (0.19 g, 0.87 mmol; This compound was synthesized according to WO2007/011065) and 2-chloro-5′-fluoro-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (intermediate 1, 0.20 g, 0.83 mmol) in tetrahydrofuran (5 mL) was added triethylamine (0.35 mL, 2.5 mmol) at room temperature. The reaction mixture was stirred for 8 hours and poured into 1N hydrochloric acid. Extraction with chloroform was performed and the organic phase was dried over anhydrous sodium sulfate. The organic solvent was removed under reduced pressure and the residue was crystallized from ethanol to afford (S)-5′-fluoro-2-[2-(4-fluoro-phenyl)-morpholin-4-yl]-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (0.25 g, 0.65 mmol, 78%) as colorless crystalline.

Workup

  1. customThis compound was synthesized
  2. extractionExtraction with chloroform
  3. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  4. customThe organic solvent was removed under reduced pressure
  5. customthe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-c59802a839a543d3bb147957fbb08cf3
Source dataset
uspto-grants-2015_01
Patent number
US08940738B2

Reaction notes

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