2,3-Dihydroxybutanedioic Acid → 5-Formyl-2-methylthiazolo[5,4-b]pyridine

HRID 2259523Notes

Reaction equation

[C:1]([C:3]1[N:8]=[C:7]2[S:9][C:10]([CH3:12])=[N:11][C:6]2=[CH:5][CH:4]=1)#N.[H-].C([Al+]CC(C)C)C(C)C.C(O)(=O)C(C(C(O)=O)O)[OH:25].[OH-].[Na+]>C1(C)C=CC=CC=1.C1COCC1>[CH:1]([C:3]1[N:8]=[C:7]2[S:9][C:10]([CH3:12])=[N:11][C:6]2=[CH:5][CH:4]=1)=[O:25]

Participants

Conditions

Temperature: -78 °C

Procedure

To a suspension of the product of Step 4 (4.42 g, 25 mmol) in 100 mL of anhyd. THF at -78° C. was added dropwise 1.5M diisobutylaluminum hydride in toluene (40 mL) and the mixture was stirred at -78° C. for 2 hr. A solution of tartaric acid 10% was then added and the mixture was stirred at room temperature for 2 hr, neutralized with 10N NaOH and extracted with EtOAc. The title product was dried over Na2SO4 and purified by flash chromatography on silica with EtOAc:hexane 20:80 to yield 3.733 g (83%) as a white solid.

Workup

stirringthe mixture was stirred at room temperature for 2 hr
extractionextracted with EtOAc
dry with materialThe title product was dried over Na2SO4
custompurified by flash chromatography on silica with EtOAc:hexane 20:80
customto yield 3.733 g (83%) as a white solid

Sources & evidence

ORD record: ord-adc2c3e1a72543cba08c76761a8a9f5f
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05472964

Reaction notes

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