Sodium Carbonate Monohydrate → HCID 178476518, compound

HRID 432208Notes

Reaction equation

HRID 432208 reaction equation
[CH2:1]([N:8]([CH2:24][CH3:25])[C:9]1[CH:14]=[CH:13][C:12](B2[O:19][C:18]([CH3:21])(C)C(C)(C)O2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:27]1[C:35]2[C:30](=[N:31][CH:32]=[N:33][C:34]=2[NH2:36])[N:29]([C@H:37]2[CH2:42][CH2:41][C@@H:40]([N:43]3[CH2:48][CH2:47][N:46]([CH3:49])[CH2:45][CH2:44]3)[CH2:39][CH2:38]2)[N:28]=1.O.[C:51](=[O:54])([O-])[O-:52].[Na+].[Na+]>COCCOC.O>[C:18]([OH:52])(=[O:19])[CH3:21].[C:51]([OH:52])(=[O:54])[CH3:1].[CH2:1]([N:8]([CH2:24][CH3:25])[C:9]1[CH:10]=[CH:11][C:12]([C:27]2[C:35]3[C:30](=[N:31][CH:32]=[N:33][C:34]=3[NH2:36])[N:29]([C@H:37]3[CH2:38][CH2:39][C@@H:40]([N:43]4[CH2:44][CH2:45][N:46]([CH3:49])[CH2:47][CH2:48]4)[CH2:41][CH2:42]3)[N:28]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 2735133Sodium Carbonate MonohydrateHCID 22347111HCID 22347111, compoundHCID 178481014HCID 178481014, compound

Product 1

HCID 178476518HCID 178476518, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of N-benzyl-N-ethyl-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine (0.065 g, 0.000193 mol), cis-3-iodo-1-[4-(4-methylpiperazino)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.071 g, 0.000161 mol), tetrakis-(triphenylphosphine)palladium (0.011 g, 0.00001 mol) and sodium carbonate monohydrate (0.056 g, 0.00045 mol) was heated in a mixture of ethylene glycol dimethyl ether (5 mL) and water (3 mL) at 80° C. for 16 hours under an atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature and solvents were removed under the reduced pressure. The residue was purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min) to yield cis-3-{4-[benzyl(ethyl)amino]phenyl}-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine diacetate (0.049 g, 0.000076 mol) as a white solid.

Workup

  1. customsolvents were removed under the reduced pressure
  2. customThe residue was purified by preparative HPLC (Hypersil C18, 8 μm, 25 cm; 10-60% acetonitrile-0.1M ammonium acetate over 25 min, 21 mL/min)

Sources & evidence

ORD record
ord-b2416f7a31de4cbbbf6f3f10981d47b8
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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