Tetrabutylammonium Fluoride → HCID 44555148, compound

HRID 2207562Notes

Reaction equation

HRID 2207562 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:7]2[C:8]3[N:16]=[N:15][N:14]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]5([O:29][Si](C)(C)C)[CH2:28][CH2:27][CH2:26][CH2:25]5)[N:19]=4)[C:9]=3[N:10]=[C:11]([NH2:13])[N:12]=2)[S:5][CH:6]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][C:2]1[N:3]=[C:4]([C:7]2[C:8]3[N:16]=[N:15][N:14]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]5([OH:29])[CH2:25][CH2:26][CH2:27][CH2:28]5)[N:19]=4)[C:9]=3[N:10]=[C:11]([NH2:13])[N:12]=2)[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66718587HCID 66718587, compound

Product 1

HCID 44555148HCID 44555148, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-(4-methylthiazol-2-yl)-3-{6-[1-trimethylsilyloxy-1-cyclopentyl]pyridin-2-ylmethyl}-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ylamine (0.105 g, 0.22 mmol) in THF (6 mL) was treated with tetrabutylammonium fluoride (1.0 M in THF, 0.33 mL, 0.33 mmol), refluxed for 90 min, cooled, concentrated in vacuo and partitioned between water and EtOAc. The aqueous phase was extracted with EtOAc and the combined organic phase dried (MgSO4), concentrated in vacuo, triturated with EtOAc and the resulting solid filtered to give the title compound (0.021 g, 24%) as a pale yellow solid.

Workup

  1. temperaturerefluxed for 90 min
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. custompartitioned between water and EtOAc
  5. extractionThe aqueous phase was extracted with EtOAc
  6. dry with materialthe combined organic phase dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customtriturated with EtOAc
  9. filtrationthe resulting solid filtered

Sources & evidence

ORD record
ord-6c823d7ac4f548ea8e95e565a4072ef2
Source dataset
uspto-grants-2016_06
Patent number
US09376443B2

Reaction notes

Loading…