1,2-Dimethoxyethane → HCID 67241889, compound

HRID 335799Notes

Reaction equation

HRID 335799 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[N:7]1[CH:12]=[C:11](B(O)O)[CH:10]=[N:9][CH:8]=1.[Br:16][C:17]1[CH:30]=[CH:29][C:28]2[O:27][C:26]3[C:21](=[CH:22][C:23](I)=[CH:24][CH:25]=3)[C:20]3([CH2:35][S:34][C:33]([NH:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[N:32]3)[C:19]=2[CH:18]=1.COCCOC>CCOC(C)=O.O>[Br:16][C:17]1[CH:30]=[CH:29][C:28]2[O:27][C:26]3[C:21](=[CH:22][C:23]([C:11]4[CH:12]=[N:7][CH:8]=[N:9][CH:10]=4)=[CH:24][CH:25]=3)[C:20]3([CH2:35][S:34][C:33]([NH:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[N:32]3)[C:19]=2[CH:18]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 67241916HCID 67241916, compound

Product 1

HCID 67241889HCID 67241889, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of sodium carbonate (1.562 g, 14.74 mmol), palladium tetrakistriphenylphosphine (0.454 g, 0.393 mmol), pyrimidin-5-ylboronic acid (0.791 g, 6.39 mmol) and 2′-bromo-N-tert-butyl-7′-iodo-5H-spiro[thiazole-4,9′-xanthen]-2-amine (2.600 g, 4.91 mmol) in a resealable pressure tube, was added DME (15 mL) and water (5 mL) at RT. The tube was sealed and heated to 80° C. After 24 hrs, the mixture was cooled to RT, diluted with EtOAc, and washed with water and brine. The organic fraction was adsorbed onto silica gel and purified by silica gel chromatography using 40% hexanes:EtOAc to afford 2′-bromo-N-tert-butyl-7′-(pyrimidin-5-yl)-5H-spiro[thiazole-4,9′-xanthen]-2-amine MS: MH+=481.0/483.0.

Workup

  1. customThe tube was sealed
  2. temperaturethe mixture was cooled to RT
  3. washwashed with water and brine
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-3f148203dc394c71aa457ac2ba7a3b1f
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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