1-Methylimidazole → HCID 46701255, compound

HRID 2090300Notes

Reaction equation

HRID 2090300 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:32]=[CH:31][CH:30]=[CH:29][C:28]=1[OH:33].CN1C=CN=C1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][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

Participants

6

Reactant 4

HCID 13901-MethylimidazoleHCID 72452-ChlorophenolHCID 11430Potassium CarbonateHCID 467010484-(7-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine

Product 1

HCID 46701255HCID 46701255, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-(7-bromo-3,4-dihydroisoquinolin-2(1H)-yl)-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine (20.0 mg, 0.0496 mmol), 2-chlorophenol (0.00765 g, 0.0595 mmol, Aldrich, Cat. No. 185779), 1-methylimidazole (2.04 mg, 0.0248 mmol, Aldrich, Cat. No. M50834), Cuprous monochloride (0.245 mg, 0.00248 mmol, Aldrich, Cat. No. 229628), and potassium carbonate (13.7 mg, 0.0992 mmol) in 1,4-dioxane (0.8 mL) was heated at 140° C. overnight. The reaction mixture was cooled to r.t. and concentrated. Then the reaction mixture was dissolved in MeOH and filtered, the filtration was purified by RP-HPLC (pH=10) to afford the desired compound. LCMS(M+H)+: m/z=451.3.

Workup

  1. concentrationconcentrated
  2. dissolutionThen the reaction mixture was dissolved in MeOH
  3. filtrationfiltered
  4. filtrationthe filtration
  5. customwas purified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-d1063aafcbeb487e9797aaa318beb03d
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

Loading…