Phthalimide → 2-((5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)methyl)isoindoline-1,3-dione

HRID 1692750Notes

Reaction equation

HRID 1692750 reaction equation
Br[CH2:2][C:3]1[S:4][C:5]2[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[N:9][C:8]([Cl:17])=[N:7][C:6]=2[N:18]=1.C([O-])([O-])=O.[K+].[K+].[C:25]1(=[O:35])[NH:29][C:28](=[O:30])[C:27]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:26]12>CN(C=O)C>[Cl:17][C:8]1[N:9]=[C:10]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[S:4][C:3]([CH2:2][N:29]3[C:25](=[O:35])[C:26]4[C:27](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:28]3=[O:30])=[N:18][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 11430Potassium CarbonateHCID 576853964-(2-(Bromomethyl)-5-chlorothiazolo[4,5-d]pyrimidin-7-yl)morpholine

Product 1

HCID 576854132-((5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)methyl)isoindoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2-(bromomethyl)-5-chlorothiazolo[4,5-d]pyrimidin-7-yl)morpholine 57 in DMF was added K2CO3, and phthalimide. The resulting solution stirred 20 h at room temperature. The reaction was concentrated in vacuo and diluted with water (10 mL). The heterogeneous mixture was filtered to afford 2-((5-chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)methyl)isoindoline-1,3-dione 58.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additiondiluted with water (10 mL)
  3. filtrationThe heterogeneous mixture was filtered

Sources & evidence

ORD record
ord-cf0af27108c14e55b86e6f41a855b3fa
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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