2-Chloro-1,1,1-triethoxyethane → 2-(Chloromethyl)-5-methoxy[1,3]thiazolo[5,4-b]pyridine

HRID 1768371Notes

Reaction equation

[NH2:1][C:2]1[C:3]([SH:10])=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[Cl:11][CH2:12][C:13](OCC)(OCC)OCC>C(O)C>[Cl:11][CH2:12][C:13]1[S:10][C:3]2[C:2]([N:1]=1)=[CH:7][CH:6]=[C:5]([O:8][CH3:9])[N:4]=2

Participants

Conditions

Temperature: 90 °C

Procedure

3-Amino-6-methoxy-2-pyridinethiol (0.8 g, Maybridge Co.) and 2-chloro-1,1,1-triethoxyethane (1.26 g) were combined in ethanol (5 mL) and heated at 90° C. in a sealed tube for 2 hours. The mixture was allowd to cool to room temperature and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography (2:1, dichloromethane:hexanes) to provide the title compound. 1H NMR (CDCl3, 300 MHz) δ 4.00 (3H, s), 4.88 (2H, s), 6.88 (1H, d, J=8.7 Hz), 8.10 (1H, d, J=8.7 Hz); MS (DCI/NH3) m/z 215.0 (M+H)+.

Workup

temperatureto cool to room temperature
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by flash chromatography (2:1, dichloromethane:hexanes)

Sources & evidence

ORD record: ord-5e8b6921a7dd4cd9a974b64d68be02c7
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235661B2

Reaction notes

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