Tetrabutylammonium Fluoride → HCID 50943691, compound

HRID 1484906Notes

Reaction equation

HRID 1484906 reaction equation
[Si]([O:8][CH2:9][C:10]1[S:14][C:13]([C:15]2[N:20]=[C:19]([NH:21][C:22]3[NH:26][N:25]=[C:24]([CH:27]4[CH2:29][CH2:28]4)[CH:23]=3)[C:18]([C:30]#[CH:31])=[CH:17][N:16]=2)=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH:27]1([C:24]2[NH:25][N:26]=[C:22]([NH:21][C:19]3[C:18]([C:30]#[CH:31])=[CH:17][N:16]=[C:15]([C:13]4[S:14][C:10]([CH2:9][OH:8])=[CH:11][CH:12]=4)[N:20]=3)[CH:23]=2)[CH2:29][CH2:28]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178437109HCID 178437109, compound

Product 1

HCID 50943691HCID 50943691, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(5-((tert-butyldimethylsilyloxy)methyl)thiophen-2-yl)-N-(3-cyclopropyl-1H-pyrazol-5-yl)-5-ethynylpyrimidin-4-amine (240 mg, 0.53 mmol, 1.0 eq), TBAF (694 mg, 2.66 mmol, 5.0 eq) in THF (20 ml) was stirred at room temperature for 30 min. The reaction mixture was evaporated under reduce pressure and the resulting residue was dissolved in EtOAc. The organic layers were washed with water, brine, dried (Na2SO4) and filtered. The filtrate was concentrated the residue was recrystalized by ether to give title compound (5-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-5-ethynylpyrimidin-2-yl)thiophen-2-yl)methanol (Compound 196) (39 mg, 22%). LC-MS (m/z)=338.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.74 (s, 2H), 0.92-0.97 (m, 2H), 1.94 (s, 1H), 4.67 (d, J=5.2 Hz, 2H), 4.83 (s, 1H), 5.61-5.63 (m, 1H), 6.52 (s, 1H), 7.03 (d, J=1.2 Hz, 1H), 7.72 (d, J=2.4 Hz, 1H), 8.45-8.50 (m, 2H), 12.24 (s, 1H).

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe resulting residue was dissolved in EtOAc
  3. washThe organic layers were washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated the residue
  7. customwas recrystalized by ether

Sources & evidence

ORD record
ord-43140315364a49b2bbf51dac9f96f03e
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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