Lawesson's reagent → HCID 178422991, compound

HRID 473166Notes

Reaction equation

HRID 473166 reaction equation
[F:1][C:2]([F:22])([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][N:16]=1)[C:3]1[N:12]=[C:11](O)[C:10]2[C:5](=[CH:6][C:7]([CH3:14])=[CH:8][CH:9]=2)[N:4]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>N1C=CC=CC=1>[F:1][C:2]([F:22])([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][N:16]=1)[C:3]1[N:12]=[C:11]([SH:32])[C:10]2[C:5](=[CH:6][C:7]([CH3:14])=[CH:8][CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 178422978HCID 178422978, compound

Product 1

HCID 178422991HCID 178422991, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
170 °C

Procedure

To 2-(difluoro(5-fluoropyridin-2-yl)methyl)-7-methylquinazolin-4-ol (413 mg, 1.35 mmol) were added Lawesson's reagent (820 mg, 2.03 mmol) and pyridine (3.5 mL), and the mixture was heated at 170° C. in a microwave reactor for 20 min. The mixture was partitioned between EtOAc (30 mL) and saturated aq NaHCO3 (50 mL), and the separated aqueous phase was extracted with EtOAc (2×30 mL). The combined organic layers were washed with 2N HCl and brine, dried over Na2SO4, and concentrated under reduced pressure onto Celite. The mixture was purified by silica get chromatography eluting with 0-30% EtOAc/hexanes to afford 2-(difluoro(5-fluoropyridin-2-yl)methyl)-7-methylquinazoline-4-thiol as an impure mixture (0.249 g). LCMS (ESI) m/z 322 (M+H)+.

Workup

  1. customThe mixture was partitioned between EtOAc (30 mL) and saturated aq NaHCO3 (50 mL)
  2. extractionthe separated aqueous phase was extracted with EtOAc (2×30 mL)
  3. washThe combined organic layers were washed with 2N HCl and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure onto Celite
  6. customThe mixture was purified by silica
  7. customget chromatography
  8. washeluting with 0-30% EtOAc/hexanes

Sources & evidence

ORD record
ord-899af2c8f77e4f06a94b5dc1713cbb55
Source dataset
uspto-grants-2014_01
Patent number
US08633207B2

Reaction notes

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