Sodium Carbonate Monohydrate → HCID 178476433, compound

HRID 432504Notes

Reaction equation

HRID 432504 reaction equation
[CH2:1]([O:3][C:4]1[N:8]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[O:19]C(C)(C)C(C)(C)[O:16]3)=[CH:11][CH:10]=2)[N:7]=[C:6](C)[CH:5]=1)[CH3:2].I[C:26]1[C:34]2[C:29](=[N:30][CH:31]=[N:32][C:33]=2[NH2:35])[N:28]([C@H:36]2[CH2:41][CH2:40][C@H:39]([N:42]3[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]3)[CH2:38][CH2:37]2)[N:27]=1.O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[C:15]([OH:19])(=[O:16])[CH3:12].[CH2:1]([O:3][C:4]1[N:8]([C:9]2[CH:14]=[CH:13][C:12]([C:26]3[C:34]4[C:29](=[N:30][CH:31]=[N:32][C:33]=4[NH2:35])[N:28]([C@H:36]4[CH2:41][CH2:40][C@H:39]([N:42]5[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]5)[CH2:38][CH2:37]4)[N:27]=3)=[CH:11][CH:10]=2)[N:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 3

HCID 2735133Sodium Carbonate MonohydrateHCID 22347330HCID 22347330, compoundHCID 178481015HCID 178481015, compound

Product 1

HCID 178476433HCID 178476433, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 5-ethoxy-3-methyl-1-[4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)phenyl]-1H-pyrazole (0.062 g, 0.00019 mol), trans-3-iodo-1-[4-(4-methylpiperazino)-cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.070 g, 0.000159 mol), tetrakis-(triphenylphosphine)palladium (0.011 g, 0.0000095 mol) and sodium carbonate monohydrate (0.049 g, 0.000398 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 trans-3-[4-(5-ethoxy-1H-1-pyrazolyl)phenyl]-1-[4-(4-methylpiperazino)cyclohexyl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine acetate (0.037 g, 0.000064 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-7f010a2d9b3e47bcad9811dd6636b8e9
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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