Dichloromethane → HCID 46944956, compound

HRID 2047201Notes

Reaction equation

HRID 2047201 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8](COCC[Si](C)(C)C)COCC[Si](C)(C)C)[N:5]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:4]2[N:3]=1.CC1(C)C(C)(C)OB([C:46]2[CH2:51][CH2:50][CH:49]([C:52]3[CH:53]=[N:54][N:55](COCC[Si](C)(C)C)[CH:56]=3)[CH2:48][CH:47]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O.O1CCOCC1>[NH:54]1[CH:53]=[C:52]([CH:49]2[CH2:50][CH2:51][C:46]([C:2]3[CH:7]=[C:6]([NH2:8])[N:5]4[N:25]=[CH:26][C:27]([C:28]5[CH:29]=[N:30][C:31]6[C:36]([CH:37]=5)=[CH:35][CH:34]=[CH:33][CH:32]=6)=[C:4]4[N:3]=3)=[CH:47][CH2:48]2)[CH:56]=[N:55]1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 66739651HCID 66739651, compoundHCID 86664780(5-Chloro-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-7-yl)-bis-(2-trimethylsilanyl-ethoxymethyl)-amine

Product 1

HCID 46944956HCID 46944956, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

To a 2 mL microwave vessel was charged 5-chloro-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (0.043 mmol, 23.5 mg), 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (0.047 mmol), K3PO4 (130 mmol, 27 mg), and PdCl2(dppf).CH2Cl2 (0.0043 mmol, 3.5 mg). To this mixture was added 9:1 dioxane:H2O (1 mL). The vessel was flushed with argon and heated to 160° C. for 30 minutes in microwave synthesizer. Upon completion, the reaction was concentrated in vacuo and the residue was dissolved in 1 mL TFA. This reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo and purified via reverse-phase preparatory HPLC to yield 5-(4-(1H-pyrazol-4-yl)cyclohex-1-enyl)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine as yellow solid. (m+H=408.30, retention time=3.16 min)

Workup

  1. customThe vessel was flushed with argon
  2. concentrationUpon completion, the reaction was concentrated in vacuo
  3. dissolutionthe residue was dissolved in 1 mL TFA
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. custompurified via reverse-phase preparatory HPLC

Sources & evidence

ORD record
ord-34ac0394602e46478a6bf8cb9790801c
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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