Phosphorus trichloride → HCID 18350679, compound

HRID 430511

Reaction equation

[NH2:1][C:2]1[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:9]([NH:12][C:13]1[CH:17]=[CH:16][S:15][C:14]=1[C:18](O)=[O:19])(=O)[CH3:10].P(Cl)(Cl)Cl>N1C=CC=CC=1>[CH3:10][C:9]1[N:1]([C:2]2[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=2)[C:18](=[O:19])[C:14]2[S:15][CH:16]=[CH:17][C:13]=2[N:12]=1

Participants

Conditions

Temperature: 105 °C

Procedure

To a mixture of pyridine (4 mL), 3-amino-2-chloropyridine (0.514 g, 4 mmol), and 3-acetamidothiophene-2-carboxylic acid (0.370 g, 4 mmol) was added phosphorus trichloride (0.02 mL, 2.3 mmol). The reaction was heated to 105° C. for 3 hours, cooled to ambient temperature and partitioned between ethyl acetate and water. Phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic phase was washed with water and brine, dried over sodium sulfate and concentrated to a greenish brown oil. This residue was flash chromatographed on silica gel (20×120 mm) eluting with 20-40% ethyl acetate/hexane to afford 0.350 g (63%) of 2-methyl-3-(2-chloropyrid-3-yl)-3H-thieno[3,2-d]pyrimidin-4-one as a yellow foam.

Workup

temperaturecooled to ambient temperature
custompartitioned between ethyl acetate and water
customPhases were separated
extractionthe aqueous layer was extracted with ethyl acetate
washThe combined organic phase was washed with water and brine
dry with materialdried over sodium sulfate
concentrationconcentrated to a greenish brown oil
customchromatographed on silica gel (20×120 mm)
washeluting with 20-40% ethyl acetate/hexane

Sources & evidence

ORD record: ord-2d0269e9bbed4ddebd146f92e46f6348
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06323208B1

Linked notes

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