Thiophenol → HCID 66955966, compound

HRID 1399749Notes

Reaction equation

HRID 1399749 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH:9]([CH2:14][CH2:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:30]1([SH:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCCC1>[CH3:8][C:6]1[C:5]([CH:9]([CH2:14][CH2:15][CH3:16])[C:10]([O:12][CH3:13])=[O:11])=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[N:3]=[C:2]([S:36][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:7]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 86665647Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate

Product 1

HCID 66955966HCID 66955966, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (100 mg; 0.300 mmol), cesium carbonate (294 mg; 0.901 mmol) and thiophenol (0.092 mL; 0.901 mmol) were placed in a 2 mL reaction tube and dissolved in tetrahydrofuran (0.6 mL). The tube was sealed and irradiated in a microwave oven at 130° C. for 30 min. The reaction mixture was partitioned between brine and dichloromethane, filtered over a phase separator filter (1PS) and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (5-40%) in heptane to give 57 mg (32%) of the title compound as a colorless oil.

Workup

  1. customThe tube was sealed
  2. customirradiated in a microwave oven at 130° C. for 30 min
  3. customThe reaction mixture was partitioned between brine and dichloromethane
  4. filtrationfiltered over a phase separator
  5. filtrationfilter (1PS)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (5-40%) in heptane

Sources & evidence

ORD record
ord-1b8c4b5a8d2449708a25647acd4c94a0
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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