Tetrabutylammonium Fluoride → HCID 178437113, compound

HRID 1484904Notes

Reaction equation

HRID 1484904 reaction equation
[Si]([O:8][CH2:9][CH2:10][NH:11][S:12]([C:15]1[S:16][C:17]([C:20]2[N:25]=[C:24]([NH:26][C:27]3[CH:31]=[C:30]([CH:32]4[CH2:34][CH2:33]4)[NH:29][N:28]=3)[C:23]([C:35]#[CH:36])=[CH:22][N:21]=2)=[CH:18][CH:19]=1)(=[O:14])=[O:13])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH:32]1([C:30]2[CH:31]=[C:27]([NH:26][C:24]3[C:23]([C:35]#[CH:36])=[CH:22][N:21]=[C:20]([C:17]4[S:16][C:15]([S:12]([NH:11][CH2:10][CH2:9][OH:8])(=[O:13])=[O:14])=[CH:19][CH:18]=4)[N:25]=3)[NH:28][N:29]=2)[CH2:34][CH2:33]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58169524HCID 58169524, compound

Product 1

HCID 178437113HCID 178437113, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2-(tert-butyldimethylsilyloxy)ethyl)-5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)thiophene-2-sulfonamide (100 mg, 0.18 mmol, 1 equiv.) in dry THF (4 mL) was added tetrabutylammonium fluoride (0.54 mL, 0.54 mmol, 3.0 equiv., 1.0 M solution in THF) dropwise. The reaction mixture was allowed to stir for 1 h. The reaction mixture was washed with NaHCO3 and water. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated and resulting residue was crystallized with THF, ether and ethanol to give title compound 5-(4-(3-cyclopropyl-1H-pyrazol-5-ylamino)-5-ethynylpyrimidin-2-yl)-N-(2-hydroxyethyl)thiophene-2-sulfonamide (Compound 108) as pale solid (50 mg, 64%). LC-MS (m/z)=430.9 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.75-0.76 (m, 2H), 0.98-1.00 (m, 2H), 1.95 (m, 1H), 2.95 (q, J=5.2 Hz, 2H), 3.42 (q, J=6.0 Hz, 2H), 4.75 (t, J=5.2 Hz, 1H), 4.89 (s, 1H), 6.44 (s, 1H), 7.62 (d, J=3.6 Hz, 1H), 7.83 (d, J=3.6 Hz, 1H), 8.02 (s, 1H), 8.52 (s, 1H), 8.81 (s, 1H), 12.32 (s, 1H).

Workup

  1. washThe reaction mixture was washed with NaHCO3 and water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customresulting residue
  6. customwas crystallized with THF, ether and ethanol

Sources & evidence

ORD record
ord-826489ddb4234d7cba0e078405773c91
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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