Sodium Carbonate → HCID 22346662, compound

HRID 2056167Notes

Reaction equation

HRID 2056167 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:11][CH:10]=2)O1.[NH2:27][C:28]1[N:33]=[CH:32][N:31]=[C:30]2[N:34]([CH:38]3[CH2:43][CH2:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][CH2:39]3)[N:35]=[C:36](I)[C:29]=12.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[NH2:27][C:28]1[N:33]=[CH:32][N:31]=[C:30]2[N:34]([CH:38]3[CH2:43][CH2:42][N:41]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:40][CH2:39]3)[N:35]=[C:36]([C:9]3[CH:10]=[CH:11][C:12]([NH:15][C:16]([O:17][CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[O:25])=[CH:13][CH:14]=3)[C:29]=12

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 4600564Benzyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamateHCID 22346822tert-Butyl 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate

Product 1

HCID 22346662HCID 22346662, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of benzyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (9.54 g, 0.027 mol), tert-butyl 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-piperidinecarboxylate (10.0 g, 0.0225 mol), tetrakis-(triphenylphosphine)palladium (1.56 g, 0.00135 mol) and sodium carbonate (5.97 g, 0.0563 mol) was heated in a mixture of ethylene glycol dimethyl ether (120 mL) and water (60 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 partitioned between water (150 mL) and dichloromethane (150 mL); the organic phase was washed with brine, dried with magnesium sulfate and concentrated under reduced pressure. The residue was triturated in diethyl ether and the precipitate was collected by filtration and dried to yield tert-butyl 4-[4-amino-3-(4-[(benzyloxy)carbonyl]aminophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinecarboxylate (10.1 g, 0.0186 mol) as a white solid.

Workup

  1. customsolvents were removed under the reduced pressure
  2. customThe residue was partitioned between water (150 mL) and dichloromethane (150 mL)
  3. washthe organic phase was washed with brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated in diethyl ether
  7. filtrationthe precipitate was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-e5b273be8d6044bd8719b6ba36cd5819
Source dataset
uspto-grants-2008_02
Patent number
US07332497B2

Reaction notes

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