1,2-Dimethoxyethane → HCID 59272360, compound

HRID 1970283Notes

Reaction equation

HRID 1970283 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[C:17]1[CH:30]=[CH:29][C:28]2[O:27][C:26]3[C:21](=[CH:22][C:23]([O:31][CH3:32])=[CH:24][CH:25]=3)[C:20]3([CH:36]([CH3:37])[O:35][C:34]([NH2:38])=[N:33]3)[C:19]=2[CH:18]=1.COCCOC>CCOC(C)=O.O>[CH3:32][O:31][C:23]1[CH:24]=[CH:25][C:26]2[O:27][C:28]3[C:19](=[CH:18][C:17]([C:11]4[CH:12]=[N:7][CH:8]=[N:9][CH:10]=4)=[CH:30][CH:29]=3)[C@:20]3([C@H:36]([CH3:37])[O:35][C:34]([NH2:38])=[N:33]3)[C:21]=2[CH:22]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 67242744HCID 67242744, compound

Product 1

HCID 59272360HCID 59272360, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of sodium carbonate (0.636 g, 6.00 mmol), palladium tetrakistriphenylphosphine (0.185 g, 0.160 mmol), pyrimidin-5-ylboronic acid (0.322 g, 2.60 mmol) and 2′-bromo-7′-methoxy-5-methyl-5H-spiro[oxazole-4,9′-xanthen]-2-amine (0.750 g, 1.999 mmol) in a resealable pressure tube, was added DME (6 mL) and water (2 mL) at RT. The tube was sealed and heated to 85° C. After 2 hrs, the mixture was cooled to RT, diluted with EtOAc, and washed with brine. The organic fraction was dried with sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography using 2-8% MeOH in CH2Cl2 with 1% NH4OH to afford a mixture of diastereomers as an off-white foam. [email protected] min. Purification of the resulting racemic product mixture using Chiralpack AD-H (2×15 cm) 30% MeOH/CO2, 100 bar, 70 ml/min afforded:

Workup

  1. customThe tube was sealed
  2. temperaturethe mixture was cooled to RT
  3. washwashed with brine
  4. dry with materialThe organic fraction was dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. customto afford
  8. additiona mixture of diastereomers as an off-white foam
  9. custom[email protected] min
  10. customPurification of the resulting racemic product mixture
  11. customafforded

Sources & evidence

ORD record
ord-bcd871de968f4bbd9f2cafac07d0f23d
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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