Potassium Carbonate → HCID 86705373, compound

HRID 707462Notes

Reaction equation

P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:28]=[CH:27][C:11]([CH2:12][N:13]2[C:18]3[S:19][CH:20]=[C:21]([CH3:22])[C:17]=3[C:16]3=[N:23][CH:24]=[N:25][N:15]3[C:14]2=[O:26])=[CH:10][CH:9]=1.[C:29](=O)([O-])[O-:30].[K+].[K+]>CN(C)C=O>[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][N:13]2[C:18]3[S:19][C:20]([CH:29]=[O:30])=[C:21]([CH3:22])[C:17]=3[C:16]3=[N:23][CH:24]=[N:25][N:15]3[C:14]2=[O:26])=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Phosphorus oxychloride (1.47 ml, 15.8 mmol) was added to N,N-dimethylformamide (13 ml) and the mixture was stirred for 20 minutes. 6-(4-Methoxybenzyl)-9-methylthieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (1.29 g, 3.94 mmol) was added as a solid and the mixture was heated at 90° C. for 45 minutes. The mixture was cooled to room temperature and poured into a mixture of ice (30 mL) and potassium carbonate (5 g). After the ice had melted the pH was 8-9. The mixture was extracted with dichloromethane (3×30 mL) and the combined extracts were washed with brine (30 mL), dried (MgSO4) and concentrated under vacuum. The residue was purified by flash LC (20-100% ethyl acetate in hexanes) to afford the aldehyde (0.87 g, 62%) as a yellow powder. 1H NMR (400 MHz, CDCl3) δ 3.01 (s, 3H), 3.78 (s, 3H), 5.38 (s, 2H), 6.86-6.88 (m, 2H), 7.44-7.46 (m, 2H), 8.33 (s, 1H), 10.12 (s, 1H). LCMS (MH+, 355.0).

Workup

temperatureThe mixture was cooled to room temperature
extractionThe mixture was extracted with dichloromethane (3×30 mL)
washthe combined extracts were washed with brine (30 mL)
dry with materialdried (MgSO4)
concentrationconcentrated under vacuum
customThe residue was purified by flash LC (20-100% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-4b5b114ec83e4fe78f7b10fe7259ee14
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09175010B2

Reaction notes

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