Tetrabutylammonium Fluoride → HCID 86686629, compound

HRID 627323Notes

Reaction equation

HRID 627323 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([CH3:19])([CH3:18])[C:16]#[N:17])=[CH:11][CH:10]=2)[C:5]([C:20]#[C:21][CH2:22][OH:23])=[CH:4][N:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:20]=[C:21]([CH2:22][OH:23])[N:8]([C:9]3[CH:10]=[CH:11][C:12]([C:15]([CH3:19])([CH3:18])[C:16]#[N:17])=[CH:13][CH:14]=3)[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86686628HCID 86686628, compound

Product 1

HCID 86686629HCID 86686629, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-(4-(2-chloro-5-(3-hydroxyprop-1-ynyl)pyrimidin-4-ylamino)phenyl)-2-methylpropanenitrile was reacted with a solution of 1M tetrabutylammonium fluoride in THF (5.85 mL, 5.85 mmol) diluted to 10 mL with additional dry THF for 1.5 hr at 60° C. Analytical LC indicates the reaction is complete (minimal shift in retention time). Volatiles were removed and the residue taken up into ethyl acetate. Organics were washed with water, brine then dried over sodium sulfate. Volatiles were removed and the residue purified by NPLC (10-75% ethyl acetate in Heptane, Analogix) to yield the desired product (589 mg, 68%). MS 327.3 m/z (M+H)

Workup

  1. customVolatiles were removed
  2. washOrganics were washed with water, brine
  3. dry with materialthen dried over sodium sulfate
  4. customVolatiles were removed
  5. customthe residue purified by NPLC (10-75% ethyl acetate in Heptane, Analogix)

Sources & evidence

ORD record
ord-443f202eab43414098d894697a306c62
Source dataset
uspto-grants-2016_04
Patent number
US09309252B2

Reaction notes

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