Reaction #497858

Reaction equation

product

4-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]tetrahydro-2H-thiopyran-4-ol 1,1-dioxide

Eaton's reagent

NaHCO3

→

N-{3-[2-(1,1-dioxido-3,6-dihydro-2H-thiopyran-4-yl)-1,3-thiazol-5-yl]-5-methylphenyl}-4-(trifluoromethyl)pyrimidin-2-amine

Yield 91.0%

Solvents

water

Conditions

Workup

1. 1
   Extractionextracted with EtOAc (2×15 mL)
2. 2
   WashThe combined organic layers were washed with brine
3. 3
   Dryingdried (MgSO4)
4. 4
   Otherevaporated
5. 5
   workup.ADDITIONUpon addition of CH2Cl2
6. 6
   Otherthe title compound precipitated
7. 7
   Otherwas isolated by filtration (0.185 g, 0.397 mmol, 91% yield)

Procedure

The product from Step 1 (210 mg, 0.433 mmol) was combined with Eaton's reagent (1.00 ml, 6.30 mmol) and stirred at 100° C. for 16 hrs. The reaction was cooled to room temperature and slowly neutralized with aqueous saturated NaHCO3 (4 mL). It was then diluted with water (4 mL) and extracted with EtOAc (2×15 mL). The combined organic layers were washed with brine, dried (MgSO4), and evaporated. Upon addition of CH2Cl2, the title compound precipitated and was isolated by filtration (0.185 g, 0.397 mmol, 91% yield). MS ESI: [M+H]+ m/z 467.0. 1H NMR (500 MHz, DMSO-d6) δ 10.29 (s, 1H), 8.83 (d, J=4.9, 1H), 8.12 (d, J=2.7, 1H), 8.03 (bs, 1H), 7.47 (bs, 1H), 7.29 (d, J=4.9, 1H), 7.21 (bs, 1H), 6.53 (m, 1H), 4.00 (m, 2H), 3.39 (m, 2H), 3.14 (m, 2H), 2.32 (s, 3H). rhSYK activity=+++.

Source