Tetrabutylammonium Fluoride → HCID 90310682, compound

HRID 1519179Notes

Reaction equation

HRID 1519179 reaction equation
[Si]([O:8][C:9]1[C:10]([F:28])=[C:11]([C:21]2[N:22]=[CH:23][C:24]([NH2:27])=[N:25][CH:26]=2)[CH:12]=[CH:13][C:14]=1[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[NH2:27][C:24]1[N:25]=[CH:26][C:21]([C:11]2[C:10]([F:28])=[C:9]([OH:8])[C:14]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:13][CH:12]=2)=[N:22][CH:23]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 90310809HCID 90310809, compound

Product 1

HCID 90310682HCID 90310682, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution consisting of 5-(3-((tert-butyldimethylsilyl)oxy)-4-cyclohexyl-2-fluorophenyl)pyrazin-2-amine (936 mg, 2.33 mmol) and THF (15 mL) was treated with tetrabutylammonium fluoride (5 mL, 5 mmol, 1 M in THF). The reaction mixture was stirred for 16 hours at which point it was concentrated to dryness and purified by FCC to yield the title compound (0.403 g, 60%) which was used without further purification. MS (ESI): mass calcd. for C16H18FN3O, 287.14; m/z found, 288.1 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.47-8.45 (m, 1H), 8.09 (d, J=1.5, 1H), 7.32 (m, 1H), 7.06-7.03 (m, 1H), 5.60 (d, J=6.3, 1H), 4.65 (s, 2H), 3.00-2.92 (m, 1H), 1.94-1.81 (m, 4H), 1.80-1.74 (m, 1H), 1.52-1.38 (m, 4H), 1.33-1.25 (m, 1H).

Workup

  1. concentrationwas concentrated to dryness
  2. custompurified by FCC

Sources & evidence

ORD record
ord-836bb5f91f7743a99f1bcc4dc435273c
Source dataset
uspto-grants-2015_07
Patent number
US09073876B2

Reaction notes

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