Selenium Dioxide → 5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidine-2-carbaldehyde

HRID 1365846Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[S:10][C:9]([CH3:11])=[N:8][C:6]=2[N:7]=1.[Se](=O)=[O:19]>O1CCOCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:5]2[S:10][C:9]([CH:11]=[O:19])=[N:8][C:6]=2[N:7]=1

Participants

Conditions

Temperature: 105 °C

Procedure

To a solution of 5-chloro-2-methyl-7-morpholin-4-yl-thiazolo[4,5-d]pyrimidine (102 mg, 0.38 mmol) in 1,4-dioxane (5 mL) was added selenium dioxide (51 mg, 0.46 mmol) and the solution heated at 105° C. for 6 h. The reaction mixture was cooled to RT and partitioned between DCM and brine. The organic layer was isolated, then dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by column chromatography to give the title compound as an orange solid (53 mg, 49%).

Workup

temperatureThe reaction mixture was cooled to RT
custompartitioned between DCM and brine
customThe organic layer was isolated
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe resultant residue was purified by column chromatography

Sources & evidence

ORD record: ord-812c4e3568f84045983d2aaab9f857fd
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893060B2

Reaction notes

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