Cesium carbonate → HCID 86726499, compound

HRID 1487673Notes

Reaction equation

HRID 1487673 reaction equation
[Cl:1][C:2]1[N:6]([CH2:7][CH3:8])[N:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:11]=[C:12]([O:37][CH:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)[C:13]2[C:18]([C:19]3[CH:28]=[CH:27][C:22]4[N:23]=[C:24]([CH3:26])[O:25][C:21]=4[CH:20]=3)=[CH:17][N:16](COCC[Si](C)(C)C)[C:14]=2[N:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[Cl:1][C:2]1[N:6]([CH2:7][CH3:8])[N:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:11]=[C:12]([O:37][CH:38]2[CH2:42][CH2:41][CH2:40][CH2:39]2)[C:13]2[C:18]([C:19]3[CH:28]=[CH:27][C:22]4[N:23]=[C:24]([CH3:26])[O:25][C:21]=4[CH:20]=3)=[CH:17][NH:16][C:14]=2[N:15]=1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 86726500HCID 86726500, compound

Product 1

HCID 86726499HCID 86726499, compoundYield 19.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 2724141Tetrabutylammonium FluorideSolvent

Conditions

Temperature
80 °C

Procedure

N-(5-Chloro-1-ethyl-1H-pyrazol-4 yl)-4-(cyclopentyloxy)-5-(2-methylbenzo[d]oxazol-6-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine (1 equiv) dissolved in 1 M tetrabutylammonium fluoride in THF (6.3 equiv). The mixture was stirred at 80° C. for 12 h. After cooling to room temperature, the reaction was diluted with THF (0.063 M) and cesium carbonate (5 equiv) was added. The solids were filtered and the filtrate was dried over sodium sulfate and concentrated. The crude product was purified to give the desired compound (19.7% yield). 1H NMR (400 MHz, CHLOROFORM-d1) δ ppm 8.81 (br. s, 1H), 8.13 (s, 1H), 7.81 (s, 1H), 7.62-7.56 (m, 2H), 6.91 (s, 1H), 6.30 (s, 1H), 5.68-5.65 (m, 1H), 4.18 (q, J=7.2 Hz, 2H), 2.66 (s, 3H), 1.95-1.87 (m, 4H), 1.74-1.68 (m, 2H), 1.43 (t, J=7.2 Hz, 3H). MS (ESI) m/z 478.2 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. additionwas added
  3. filtrationThe solids were filtered
  4. dry with materialthe filtrate was dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-440fabeaca9140d4b12847f06105a8e5
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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