TBAF tetrahydrofuran → HCID 178503411, compound

HRID 2420986Notes

Reaction equation

HRID 2420986 reaction equation
[CH:1]1([C:4]2[O:8][C:7]([C:9]3[C:10]([O:17]CC[Si](C)(C)C)=[N:11][C:12]([S:15][CH3:16])=[N:13][CH:14]=3)=[N:6][N:5]=2)[CH2:3][CH2:2]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>C1COCC1>[CH:1]1([C:4]2[O:8][C:7]([C:9]3[C:10]([OH:17])=[N:11][C:12]([S:15][CH3:16])=[N:13][CH:14]=3)=[N:6][N:5]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 11078149TBAF tetrahydrofuranHCID 67251162HCID 67251162, compound

Product 1

HCID 178503411HCID 178503411, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(5-Cyclopropyl[1,3,4]oxadiazol-2-yl)-4-(2-trimethylsilylethoxy)-2-methylthiopyrimidine (10.0 g) obtained in Step 5 was dissolved in THF (100 mL), and a TBAF-THF solution (1.0 mol/L, 42.8 mL) was added thereto. The mixture was stirred at room temperature for 12 hours. After completion of the reaction was confirmed by thin-layer chromatography, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography. The fraction of the desired product was collected, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to precipitate crystals. The resulting crystals were collected by filtration and dried thoroughly under reduced pressure to give 5-(5-cyclopropyl[1,3,4]oxadiazol-2-yl)-4-hydroxy-2-methylthiopyrimidine [Compound (AB) in which —X—Y—Z— represents —O—C(c-C3H5)═N—, and R2B is methylthio] (6.26 g, yield 88%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel chromatography
  3. customThe fraction of the desired product was collected
  4. customthe solvent was evaporated under reduced pressure
  5. additionDiisopropyl ether was added to the residue
  6. customto precipitate crystals
  7. filtrationThe resulting crystals were collected by filtration
  8. customdried thoroughly under reduced pressure

Sources & evidence

ORD record
ord-311037fbb9b3405888c1c096cc3beba5
Source dataset
uspto-grants-2011_06
Patent number
US07956060B2

Reaction notes

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