Phthalimide → 2-((3-(3-fluorophenyl)-6-methyl-4-oxo-4H-pyrido-[1,2-a]pyrimidin-2-yl)methyl)isoindoline-1,3-dione

HRID 405957Notes

Reaction equation

HRID 405957 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13](=[O:14])[N:12]3[C:15]([CH3:19])=[CH:16][CH:17]=[CH:18][C:11]3=[N:10][C:9]=2[CH2:20]O)[CH:5]=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:41]1(=[O:51])[NH:45][C:44](=[O:46])[C:43]2=[CH:47][CH:48]=[CH:49][CH:50]=[C:42]12.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13](=[O:14])[N:12]3[C:15]([CH3:19])=[CH:16][CH:17]=[CH:18][C:11]3=[N:10][C:9]=2[CH2:20][N:45]2[C:41](=[O:51])[C:42]3[C:43](=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:44]2=[O:46])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 668313583-(3-fluorophenyl)-2-(hydroxymethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Product 1

HCID 668313462-((3-(3-fluorophenyl)-6-methyl-4-oxo-4H-pyrido-[1,2-a]pyrimidin-2-yl)methyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3-fluorophenyl)-2-(hydroxymethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (0.05110 g, 0.180 mmol) in THF (3.00 mL) was added triphenylphosphine (0.141 g, 0.539 mmol), phthalimide (0.0793 g, 0.539 mmol), and diisopropyl azodicarboxylate (0.106 mL, 0.539 mmol). The reaction mixture was stirred at rt. After 3 h, the mixture was concd under reduced pressure and partitioned between EtOAc (100 mL) and brine (100 mL). The organic layer was dried over Na2SO4, filtered, and concd under reduced pressure. The residue was purified by silica gel column chromatography on a 40 g Redi-Sep™ column using 0 to 50% gradient of EtOAc in hexane over 14 min and 50% isocratic of EtOAc for 15 min as eluent to give 2-((3-(3-fluorophenyl)-6-methyl-4-oxo-4H-pyrido-[1,2-a]pyrimidin-2-yl)methyl)isoindoline-1,3-dione as a solid: Mass Spectrum (ESI) m/e=414.1 (M+1).

Workup

  1. custompartitioned between EtOAc (100 mL) and brine (100 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customThe residue was purified by silica gel column chromatography on a 40 g Redi-Sep™ column
  5. customover 14 min

Sources & evidence

ORD record
ord-cdfe647fc59642c1b42fdb252800f6eb
Source dataset
uspto-grants-2014_06
Patent number
US08754089B2

Reaction notes

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