Tetrabutylammonium Fluoride → 3-Methoxy-4-((5-(2-methylbenzo[d]oxazol-6-yl)-4-(1-methylcyclobutoxy)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-N-(oxetan-3-yl)benzamide

HRID 1487655Notes

Reaction equation

HRID 1487655 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[NH:16][C:17]1[N:18]=[C:19]([O:44][C:45]2([CH3:49])[CH2:48][CH2:47][CH2:46]2)[C:20]2[C:25]([C:26]3[CH:35]=[CH:34][C:29]4[N:30]=[C:31]([CH3:33])[O:32][C:28]=4[CH:27]=3)=[CH:24][N:23](COCC[Si](C)(C)C)[C:21]=2[N:22]=1)[C:6]([NH:8][CH:9]1[CH2:12][O:11][CH2:10]1)=[O:7].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[NH:16][C:17]1[N:18]=[C:19]([O:44][C:45]2([CH3:49])[CH2:48][CH2:47][CH2:46]2)[C:20]2[C:25]([C:26]3[CH:35]=[CH:34][C:29]4[N:30]=[C:31]([CH3:33])[O:32][C:28]=4[CH:27]=3)=[CH:24][NH:23][C:21]=2[N:22]=1)[C:6]([NH:8][CH:9]1[CH2:10][O:11][CH2:12]1)=[O:7]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 867264863-Methoxy-4-((5-(2-methylbenzo[d]oxazol-6-yl)-4-(1-methylcyclobutoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-N-(oxetan-3-yl)benzamide

Product 1

HCID 867264873-Methoxy-4-((5-(2-methylbenzo[d]oxazol-6-yl)-4-(1-methylcyclobutoxy)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-N-(oxetan-3-yl)benzamideYield 17%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
90 °C

Procedure

A mixture of 3-methoxy-4-((5-(2-methylbenzo[d]oxazol-6-yl)-4-(1-methylcyclobutoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)-N-(oxetan-3-yl)benzamide (1 equiv) in THF (0.1 M) in a sealed tube was added a solution of tetrabutylammonium fluoride in THF (1 M, 10 equiv). The resulting mixture was heated at 90° C. for 16 h. The reaction mixture was cooled to room temperature and concentrated. The residue was purified to afford the title compound (17% yield over two steps). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.82 (s, 1H), 8.97 (d, J=6.4 Hz, 1H), 8.58 (d, J=8.0 Hz, 1H), 7.97 (d, J=0.8 Hz, 1H), 7.68-7.54 (m, 5H), 7.38 (d, J=2.4 Hz, 1H), 5.06-5.00 (m, 1H), 4.79 (t, J=7.0 Hz, 2H), 4.62 (t, J=6.4 Hz, 2H), 3.98 (s, 3H), 2.62 (s, 3H), 2.49-2.43 (m, 2H), 2.32-2.27 (m, 2H), 1.87-1.78 (m, 2H), 1.75 (s, 3H). MS (ESI) m/z 555.3 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was purified

Sources & evidence

ORD record
ord-2f49f47a8ad44e0b951cdd9a351df9fe
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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