Phthalimide → HCID 58796945, compound

HRID 405987Notes

Reaction equation

HRID 405987 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[N:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]2=[N:4][C:3]=1[CH:13](O)[CH3:14].[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:1][C:2]1[C:7](=[O:8])[N:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]2=[N:4][C:3]=1[CH:13]([N:20]1[C:16](=[O:26])[C:17]2[C:18](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:19]1=[O:21])[CH3:14]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 66831356HCID 66831356, compound

Product 1

HCID 58796945HCID 58796945, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 500 mL of round-bottom flask was charged with 3-bromo-2-(1-hydroxyethyl)-4H-pyrido[1,2-a]pyrimidin-4-one (0.76 g, 2.86 mmol), phthalimide (0.504 g, 3.43 mmol) and PPh3 (0.899 g, 3.43 mmol) in THF (20 mL) followed by the dropwise addition of diisopropylazodicarboxylate (0.675 g, 3.43 mmol) in THF (3 mL). The reaction mixture was stirred overnight at rt. After the completion of the reaction, monitored by TLC, the reaction mass was cond under vacuum and purified by silica gel column chromatography using 5 to 35% EtOAc in hexane to provide 2-(1-(3-bromo-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)ethyl)isoindoline-1,3-dione as light yellow solid: 1HNMR (400 MHz, DMSO-d6): δ8.95-8.96 (dd,1H), 8.00-8.06 (m,1H), 7.8 (s,4H), 7.5-7.6 (m,2H), 7.4 (d,1H), 5.6 (q,1H), 1.84 (d,3H).

Workup

  1. customAfter the completion of the reaction
  2. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-1b62055a3a924f0e9e7f1f8b5f9d963e
Source dataset
uspto-grants-2014_06
Patent number
US08754089B2

Reaction notes

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