Tetrahydrofuran → HCID 66831342, compound

HRID 405989Notes

Reaction equation

HRID 405989 reaction equation
CS[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]2=[N:11][C:10]=1[CH:20]([N:22]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:32])[CH3:21].O[O:34][S:35]([O-:37])=O.[K+].[CH2:39]1COCC1>O>[CH3:39][S:35]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:3][C:4]=1[C:9]1[C:14](=[O:15])[N:13]2[CH:16]=[CH:17][CH:18]=[CH:19][C:12]2=[N:11][C:10]=1[CH:20]([N:22]1[C:23](=[O:32])[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:30]1=[O:31])[CH3:21])(=[O:37])=[O:34]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 66831367HCID 66831367, compound

Product 1

HCID 66831342HCID 66831342, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 2-(1-(3-(2-(methylthio)phenyl)-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)ethyl)isoindoline-1,3-dione (0.4278 g, 0.969 mmol) in THF (7.27 mL) and water (2.422 mL) was added oxone (1.489 g, 2.422 mmol) and the mixture was stirred at rt. After 24 h, LC-MS (ESI) and HPLC showed that the reaction was complete and no reactant remained. After 26 h, to the mixture was added water (50 mL) and the resulting precipitate was filtered and washed with water (50 mL) to give 2-(1-(3-(2-(methylsulfonyl)phenyl)-4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl)ethyl)isoindoline-1,3-dione as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.99 (1 H, ddd, J=7.0, 1.6, 0.8 Hz), 8.01-8.11 (2 H, m), 7.69-7.86 (5 H, m), 7.56 (1 H, td, J=7.8, 1.3 Hz), 7.46 (1 H, td, J=6.9, 1.4 Hz), 7.29 (1 H, td, J=7.5, 1.4 Hz), 7.09 (1 H, dd, J=7.6, 1.2 Hz), 5.37-5.46 (1 H, m), 3.03 (3 H, s), 1.60 (3 H, d, J=7.0 Hz); Mass Spectrum (ESI) a major peak of m/e=474.1 (M+1).

Workup

  1. waitAfter 26 h
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with water (50 mL)

Sources & evidence

ORD record
ord-c57572575cde468aac333b1ea119ea1f
Source dataset
uspto-grants-2014_06
Patent number
US08754089B2

Reaction notes

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