HCID 59402391, compound → HCID 59402345, compound

HRID 2090384Notes

Reaction equation

HRID 2090384 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([CH2:26][O:27][Si](C(C)(C)C)(C)C)[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.F[Si-2](F)(F)(F)(F)F.[H+].[H+]>O1CCOCC1.O>[NH2:25][C:14]1[N:13]=[C:12]([N:8]2[CH:7]([CH2:26][OH:27])[CH2:6][C:5]3[C:10](=[CH:11][C:2]([Br:1])=[CH:3][CH:4]=3)[CH2:9]2)[CH:17]=[C:16]([N:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)[N:15]=1

Participants

4

Reactant 1

HCID 59402391HCID 59402391, compound

Product 1

HCID 59402345HCID 59402345, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-[7-bromo-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3,4-dihydroisoquinolin-2(1H)-yl]-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine (150 mg, 0.27 mmol) in 1,4-dioxane (3 mL) was added 1.7 M of fluorosilicic acid in water (480 uL). The reaction mixture was stirred at r.t. for 2 h., and then concentrated to remove dioxane. The residue was dissolved in MeOH and purified by RP-HPLC (pH=10) to afford the desired compound. LCMS(M+H)+: m/z=433.2.

Workup

  1. concentrationconcentrated
  2. customto remove dioxane
  3. dissolutionThe residue was dissolved in MeOH
  4. custompurified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-598eb257e1f9453eb04f2d84f0ffd8d8
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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