Potassium Carbonate → 5-(Pyridin-2-ylsulfanyl)-thiazol-2-ylamine

HRID 416251Notes

Reaction equation

Br.[NH2:2][C:3]1[S:4][C:5](Br)=[CH:6][N:7]=1.[SH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[S:9][C:5]1[S:4][C:3]([NH2:2])=[N:7][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-amino-5-bromothiazole hydrobromide (1.00 g, 3.85 mmol) in DMF (8 mL) was added 2-mercaptopyridine (428 mg, 3.85 mmol) followed by addition of powdered K2CO3 (1.81 g, 15.09 mmol). The mixture was stirred at 80° C. for 1 h and at rt for 16 h. The solvent was removed in vacuo at 80° C. and the compound was partitioned between H2O and EtOAc. The aqueous layer was extracted with EtOAc and the organic phase was extracted with HCl 1N. The acidic extract was neutralized with saturated NaHCO3 and the precipitate was extracted with EtOAc, washed with brine, dried over MgSO4 and concentrated in vacuo to afford the title compound 169 (589 mg, 73% yield). 1H NMR: (Acetone-d6) δ(ppm): 8.36 (s, 1H), 7.66 (s, 1H), 7.20 (s, 1H), 7.12-7.05 (m, 2H), 6.84 (s, 2H). m/z: 210.1 (MH+).

Workup

customThe solvent was removed in vacuo at 80° C.
customthe compound was partitioned between H2O and EtOAc
extractionThe aqueous layer was extracted with EtOAc
extractionthe organic phase was extracted with HCl 1N
extractionThe acidic extract
extractionthe precipitate was extracted with EtOAc
washwashed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c96fd53be5a949d58f2c224b04e5f97e
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088805B2

Reaction notes

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