Sodium Carbonate Monohydrate → HCID 178476628, compound

HRID 432337Notes

Reaction equation

HRID 432337 reaction equation
[C:1]1([CH:7]2[O:11][C:10](=[O:12])[N:9]([C:13]3[CH:18]=[CH:17][C:16](B4[O:23][C:22]([CH3:25])(C)C(C)(C)O4)=[CH:15][CH:14]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:29]1[C:37]2[C:32](=[N:33][CH:34]=[N:35][C:36]=2[NH2:38])[N:31]([C@H:39]2[CH2:44][CH2:43][C@@H:42]([N:45]3[CH2:50][CH2:49][N:48]([CH3:51])[CH2:47][CH2:46]3)[CH2:41][CH2:40]2)[N:30]=1.O.C(=O)([O-])[O-:54].[Na+].[Na+]>COCCOC.O>[C:22]([OH:54])(=[O:23])[CH3:25].[NH2:38][C:36]1[N:35]=[CH:34][N:33]=[C:32]2[N:31]([C@H:39]3[CH2:44][CH2:43][C@@H:42]([N:45]4[CH2:46][CH2:47][N:48]([CH3:51])[CH2:49][CH2:50]4)[CH2:41][CH2:40]3)[N:30]=[C:29]([C:16]3[CH:15]=[CH:14][C:13]([N:9]4[CH2:8][CH:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[O:11][C:10]4=[O:12])=[CH:18][CH:17]=3)[C:37]=12

Participants

6

Reactant 3

HCID 2735133Sodium Carbonate MonohydrateHCID 22347159HCID 22347159, compoundHCID 178481014HCID 178481014, compound

Product 1

HCID 178476628HCID 178476628, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 5-phenyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-oxazolan-2-one (0.085 g, 0.000233 mol), cis-3-iodo-1-[4-(4-methylpiperazino)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.086 g, 0.000194 mol), tetrakis-(triphenylphosphine)palladium (0.013 g, 0.000012 mol) and sodium carbonate monohydrate (0.060 g, 0.000485 mol) was heated in a mixture of ethylene glycol dimethyl ether (5 mL) and water (3 mL) at 80° C. for sixteen 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-0.1 M ammonium acetate over 25 min, 21 mL/min) to yield cis-3-(4-{4-amino-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}phenyl)-5-phenyl-1,3-oxazolan-2-one acetate (0.074 g, 0.000121 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-0.1 M ammonium acetate over 25 min, 21 mL/min)

Sources & evidence

ORD record
ord-9a92dce1dadc462f948969e609d138d6
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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