Tetrahydrofuran → HCID 86705397, compound

HRID 926127Notes

Reaction equation

HRID 926127 reaction equation
[C:1]([C:4]1[CH:13]=[N:12][C:11]2[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:9](=[O:23])[N:8]3[N:24]=[CH:25][N:26]=[C:7]3[C:6]=2[CH:5]=1)(=[O:3])C.C1COCC1.C[Si](C)(C)[C:34]([F:37])([F:36])[F:35].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(=O)(O)[O-].[Na+]>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][N:10]2[C:11]3[N:12]=[CH:13][C:4]([CH:1]([OH:3])[C:34]([F:37])([F:36])[F:35])=[CH:5][C:6]=3[C:7]3=[N:26][CH:25]=[N:24][N:8]3[C:9]2=[O:23])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 552549(Trifluoromethyl)trimethylsilane2×HCID 2724141Tetrabutylammonium Fluoride2×HCID 86705394HCID 86705394, compound

Product 1

HCID 86705397HCID 86705397, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

9-Acetyl-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (Example 81, 254 mg, 0.76 mmol), THF (1.3 mL) and 2 M trimethyl(trifluoromethyl)silane in THF (0.45 mL, 0.91 mmol) were combined and stirred for 10 minutes. A 2 M solution of tetrabutylammonium fluoride in THF (75 μl, 0.08 mmol) was added and stirring was continued for 3 days. Additional trimethyl(trifluoromethyl)silane (0.45 mL, 0.91 mmol) and tetrabutylammonium fluoride (75 μl, 0.08 mmol) was added and the mixture was stirred for 4 h. The reaction mixture was diluted with aqueous sodium bicarbonate (5 mL) and extracted with EtOAc (2×10 mL). The combined extracts were concentrated under vacuum. Purification (FCC, SiO2, 10 to 100%, EtOAc/hexanes) afforded the title compound (154 mg, 48%) as a white powder. 1H NMR (400 MHz, CDCl3+DMSO-d6) δ 3.27 (s, 3H), 4.80 (q, J=6.90 Hz, 1H), 5.24 (s, 2H), 6.33 (d, J=8.66 Hz, 2H), 7.05 (d, J=8.53 Hz, 2H), 7.91 (s, 1H), 8.32 (s, 1H), 8.39 (s, 1H). [M+H]=406.1.

Workup

  1. stirringstirring
  2. waitwas continued for 3 days
  3. stirringthe mixture was stirred for 4 h
  4. extractionextracted with EtOAc (2×10 mL)
  5. concentrationThe combined extracts were concentrated under vacuum
  6. customPurification (FCC, SiO2, 10 to 100%, EtOAc/hexanes)

Sources & evidence

ORD record
ord-a0e162c94b54465d863af7d7c01e022a
Source dataset
uspto-grants-2016_03
Patent number
US09284335B2

Reaction notes

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