Potassium Carbonate → HCID 46701189, compound

HRID 2090297Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:12]3[CH:17]=[C:16]([N:18]4[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]4)[N:15]=[C:14]([NH2:25])[N:13]=3)[CH2:9]2)=[CH:4][CH:3]=1.[Cl:26][C:27]1[CH:28]=[N:29][NH:30][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].CN[C@H]1CCCC[C@@H]1NC>O1CCOCC1.[Cu]I>[Cl:26][C:27]1[CH:28]=[N:29][N:30]([C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][N:8]([C:12]4[CH:17]=[C:16]([N:18]5[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]5)[N:15]=[C:14]([NH2:25])[N:13]=4)[CH2:9]3)=[CH:4][CH:3]=2)[CH:31]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 4-(7-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine (20 mg, 0.05 mmol, Example 1), 4-chloro-1H-pyrazole (6.1 mg, 0.060 mmol, Astatech, Cat. No. 64527) in 1,4-dioxane (1 mL), potassium carbonate (14 mg, 0.10 mmol), (1S,2S)-N,N′-dimethylcyclohexane-1,2-diamine (1.4 mg, 0.0099 mmol, Aldrich, Cat. No. 633089), and Copper(I) iodide (0.94 mg, 0.0050 mmol, Aldrich, Cat. No. 215554) were added. The mixture was degassed with nitrogen and heated at 120° C. overnight. The reaction mixture was concentrated. The residue was dissolved in MeOH, and purified by RP-HPLC (pH=10) to afford the desired compound. LCMS(M+H)+: m/z=425.3.

Workup

addition215554) were added
customThe mixture was degassed with nitrogen
concentrationThe reaction mixture was concentrated
dissolutionThe residue was dissolved in MeOH
custompurified by RP-HPLC (pH=10)

Sources & evidence

ORD record: ord-680a57275c6146efb181b2d0e189bcc3
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436008B2

Reaction notes

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