Stannane, tributyl(1-ethoxyethenyl)- → HCID 66733551, compound

HRID 2047165Notes

Reaction equation

HRID 2047165 reaction equation
Br[C:2]1[C:3]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)=[N:4][C:5]2[N:6]([N:25]=[CH:26][C:27]=2[C:28]2[CH:29]=[N:30][C:31]3[C:36]([CH:37]=2)=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:7]=1[N:8](COCC[Si](C)(C)C)COCC[Si](C)(C)C.C([Sn](CCCC)(CCCC)[C:49]([O:51]CC)=[CH2:50])CCC>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:8][C:7]1[N:6]2[N:25]=[CH:26][C:27]([C:28]3[CH:29]=[N:30][C:31]4[C:36]([CH:37]=3)=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:5]2[N:4]=[C:3]([N:38]2[CH2:39][CH2:40][O:41][CH2:42][CH2:43]2)[C:2]=1[C:49](=[O:51])[CH3:50]

Participants

5

Reactant 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 66733274HCID 66733274, compound

Product 1

HCID 66733551HCID 66733551, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A degassed mixture of 6-bromo-5-morpholino-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (141 mg, 0.20 mmoL), tributyl(1-ethoxyvinyl)tin (112 mg, 0.31 mmoL), Pd(PPh3)4 (24 mg, 0.02 mmoL) in Dioxane (4 mL) was heated at 100° C. for 2 days. The mixture was cooled to room temperature and filtered through short plug of 10% KF/SiO2. The crude Stille coupling product obtained after concentrating the filtrate was then treated with 3 mL of 1:1 mixture of TFA and H2O at room temperature for 30 min. Concentration and purification by prep-LC afforded 1-(7-amino-5-morpholino-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-6-yl)ethanone. LCMS tR=3.32 Min. Mass calculated for, M+ 388.1, observed LC/MS m/z 389.1 (M+H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through short plug of 10% KF/SiO2
  3. customThe crude Stille coupling product obtained
  4. concentrationafter concentrating the filtrate
  5. additionwas then treated with 3 mL of 1:1 mixture of TFA and H2O at room temperature for 30 min
  6. concentrationConcentration and purification

Sources & evidence

ORD record
ord-d48bb12f5d0f47bcb6a87c6c96871706
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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