Potassium Hydroxide → HCID 22617853, compound

HRID 842023Notes

Reaction equation

HRID 842023 reaction equation
C(OC(=O)[N:7]([CH2:14][CH2:15][NH:16][C:17]1[N:22]2[N:23]=[C:24]([CH3:40])[C:25]([C:26]3[C:31]([Cl:32])=[CH:30][C:29]([C:33]#[C:34][Si](C)(C)C)=[CH:28][C:27]=3[Cl:39])=[C:21]2[N:20]=[C:19]([CH3:41])[CH:18]=1)[CH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)(C)(C)C.[OH-].[K+]>C(O)C>[Cl:39][C:27]1[CH:28]=[C:29]([C:33]#[CH:34])[CH:30]=[C:31]([Cl:32])[C:26]=1[C:25]1[C:24]([CH3:40])=[N:23][N:22]2[C:17]([NH:16][CH2:15][CH2:14][NH:7][CH:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)=[CH:18][C:19]([CH3:41])=[N:20][C:21]=12

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 69967398HCID 69967398, compound

Product 1

HCID 22617853HCID 22617853, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of {2-[3-(2,6-dichloro-4-trimethylsilanylethynyl-phenyl)-2,5-dimethyl-pyrazolo[1,5-a]pyrimidin-7-ylamino]-ethyl}-(tetrahydro-pyran-4-yl)-carbamic acid tert-butyl ester (1.2 g, 2.0 mmol) in ethanol (2 mL) was added KOH (0.2 g, 8 mmol). After 1 hour, the reaction was cooled to 0° C. and 1:1 ethanol/concentrated aqueous hydrochloric acid (4 mL) was added and the mixture was allowed to warm to room temperature. After 1 day, the reaction was concentrated under reduced pressure, extracted from saturated aqueous sodium bicarbonate with methylene chloride, the combined extracts were dried (Na2SO4), concentrated under reduced pressure, and then chromatographed (4:1 to 10:3 to 3:2 ethyl acetate/methanol) to afford the title compound (0.70 g, 78%) as an off-white solid: +APcI MS (M+1)+458; 1H NMR (methanol-d4) δ: 7.58 (d, 1H), 6.10 (s, 1H), 3.76 (s, 1H), 2.39 (s, 3H), 2.23 (s, 3H).

Workup

  1. temperatureto warm to room temperature
  2. waitAfter 1 day
  3. concentrationthe reaction was concentrated under reduced pressure
  4. extractionextracted from saturated aqueous sodium bicarbonate with methylene chloride
  5. dry with materialthe combined extracts were dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customchromatographed (4:1 to 10:3 to 3:2 ethyl acetate/methanol)

Sources & evidence

ORD record
ord-4ef7d816d0cf471d9e24e07398b7b1d9
Source dataset
uspto-grants-2002_04
Patent number
US06372743B1

Reaction notes

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