Tetrabutylammonium Fluoride → HCID 58169324, compound

HRID 1484862Notes

Reaction equation

HRID 1484862 reaction equation
[Si]([O:8][CH2:9][C:10]1[C:11]([NH:22][C:23]2[CH:27]=[C:26]([CH:28]3[CH2:30][CH2:29]3)[NH:25][N:24]=2)=[N:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:14][CH:15]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH:28]1([C:26]2[NH:25][N:24]=[C:23]([NH:22][C:11]3[C:10]([CH2:9][OH:8])=[CH:15][N:14]=[C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[N:12]=3)[CH:27]=2)[CH2:29][CH2:30]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58169438HCID 58169438, compound

Product 1

HCID 58169324HCID 58169324, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 5-((tert-butyldimethylsilyloxy)methyl)-N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-phenylpyrimidin-4-amine (50 mg, 0.119 mmol, 1.0 eq) in anhydrous THF (2 mL), TBAF (0.5 mL, 0.5 mmol, 4.2 equiv., 1M in THF) was added dropwise. The reaction mixture was stirred at 20° C. for 2 h and then concentrated to give a residue. The residue was purified by silica gel chromatography (CH2Cl2/MeOH 500:1 to 20:1 as eluent) to afford title compound (4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-2-phenylpyrimidin-5-yl)methanol (Compound 123) (10 mg, 27.4%) as yellowish solid. LC-MS (m/z)=308.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.74-0.75 (m, 2H), 0.97-0.99 (m, 2H), 1.96-1.98 (m, 1H), 4.59 (s, 2H), 5.63 (s, 1H), 6.56 (s, 1H), 7.51 (m, 3H), 8.32 (m, 3H), 8.83 (s, 1H), 12.15 (s, 1H).

Workup

  1. concentrationconcentrated
  2. customto give a residue
  3. customThe residue was purified by silica gel chromatography (CH2Cl2/MeOH 500:1 to 20:1 as eluent)

Sources & evidence

ORD record
ord-ab86d894790d4a4887a8894605d7f03d
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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