1,2-Dimethoxyethane → HCID 59224670, compound

HRID 1811715Notes

Reaction equation

HRID 1811715 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:23])=[C:13](B2OCC(C)(C)CO2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:24][C:25]1[N:30]=[C:29](Cl)[CH:28]=[C:27]([Cl:32])[N:26]=1.C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:23])=[C:13]([C:29]2[CH:28]=[C:27]([Cl:32])[N:26]=[C:25]([NH2:24])[N:30]=2)[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 655222-Amino-4,6-dichloropyrimidineHCID 59224667HCID 59224667, compound

Product 1

HCID 59224670HCID 59224670, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

2-(5-Benzyloxy-2-methylphenyl)-5,5-dimethyl[1,3,2]dioxaborinane (41.5 g) obtained in Step 2 above, 2-amino-4,6-dichloropyrimidine (13.8 g, 84.2 mmol), and dichloroditriphenylphosphine palladium (5.0 g, 7.12 mmol) were placed in a reaction vessel, and then dimethoxyethane (800 ml) and 2N aqueous sodium carbonate solution (63.1 ml, 126.2 mmol) were sequentially added thereto. The resulting mixture was stirred at 85° C. for 4 hours. After cooling to room temperature, the reaction solution was diluted with ethyl acetate (1000 ml), and washed with water (600 ml) and then with a saturated aqueous sodium chloride solution (60 ml). The ethyl acetate solution was dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=6:1 to 3:1) to yield 4-(5-benzyloxy-2-methylphenyl)-6-chloropyrimidin-2-ylamine (10.84 g, 40%) as a pale yellow solid material.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water (600 ml)
  3. dry with materialThe ethyl acetate solution was dried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting crude product was purified by silica gel column chromatography (developing solvent: n-hexane:ethyl acetate=6:1 to 3:1)

Sources & evidence

ORD record
ord-174e3eb7f98943e4a9c0be98ca70f80a
Source dataset
uspto-grants-2013_01
Patent number
US08362236B2

Reaction notes

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