Potassium Carbonate → HCID 69518541, compound

HRID 855020Notes

Reaction equation

HRID 855020 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[O:9][CH:8]([C:14]([F:17])([F:16])[F:15])[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:6]2)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:30]1[CH:35]=[CH:34][N:33]=[C:32]([S:36][CH3:37])[N:31]=1>[Cl-].[Na+].O>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:30]1[CH:35]=[CH:34][N:33]=[C:32]([S:36][CH3:37])[N:31]=1)[O:9][CH:8]([C:14]([F:15])([F:16])[F:17])[C:7]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:6]2)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 971134-Chloro-2-methylthiopyrimidineHCID 58934952HCID 58934952, compound

Product 1

HCID 69518541HCID 69518541, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
130 °C

Procedure

To the mixture of 172 mg (0.54 mmol) of Ethyl 6-ethyl-7-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate and 320 mg (1.95 mmol) of potassium carbonate in 3 mL of anhydrous dimethylformmamide was added 270 uL (2.3 mmol) of 4-chloro-2-methylthiopyrimidine. The mixture was heated at 130° C. for half an hour. After cooling to room temperature, the reaction was dumped into 50 mL of brine, the product was extracted with ethyl acetate. The combined organic phases were washed with brine, and dried over anhydrous magnesium sulfate. After removing the volatiles, the residue was purified by silica chromatography with 1:9 EtOAc/Hexane (1:9) to afford 102 mg (43%) of a yellow solid: 1H NMR (CDCl3/400 MHz) 8.35(d, 5.2 Hz, 1H), 7.72(s, 1H), 7.13(s, 1H), 6.74(s, 1H), 6.54(d, J=5.6 Hz, 1H), 5.66(q, J=6.8 Hz, 1H), 4.30(m, 2H), 2.45(q, J=7.6 Hz, 2H), 2.27(s, 3H), 1.33(t, J=7.2 Hz, 3H), 1.12(t, J=7.6 Hz, 3H); MS (ESI+) 441 (M+1, 100).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe product was extracted with ethyl acetate
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removing the volatiles
  6. customthe residue was purified by silica chromatography with 1:9 EtOAc/Hexane (1:9)

Sources & evidence

ORD record
ord-9561a3c9b6224ec694c1aa941d4468fc
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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