Toluene → HCID 66750107, compound

HRID 75435Notes

Reaction equation

HRID 75435 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:14][CH:13]3[O:15][CH:10]([CH2:11][CH2:12]3)[CH2:9]2)[CH:5]=[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:3]=1.CC1(C)C(C)(C)OB([C:30]2[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=2)O1.C([O-])([O-])=O.[Na+].[Na+].C1(C)C=CC=CC=1>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCCCCC.CCOC(C)=O.CCO>[CH:10]12[O:15][CH:13]([CH2:12][CH2:11]1)[CH2:14][N:8]([C:6]1[CH:5]=[C:4]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:3]=[C:2]([C:30]3[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=3)[N:7]=1)[CH2:9]2

Participants

9

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 866658943-(2-Chloro-6-phenylpyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane2×

Product 1

HCID 66750107HCID 66750107, compoundYield 75.6%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 3-(2-chloro-6-phenylpyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane (500 mg, 1.66 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (545 mg, 2.49 mmol), Pd(PPh3)4 (20 mg), and 2M aqueous Na2CO3 (1.25 mL) in 1:1 toluene:EtOH (8 mL) was heated in a microwave at 120° C. for 20 min. The reaction was repeated with 386 mg of 3-(2-chloro-6-phenylpyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane. The reaction mixtures were combined, diluted with EtOAc and washed with H2O then brine. The organic layer was dried over MgSO4 and concentrated in vacuo to give an orange oil. Silica gel chromatography (hexane/EtOAc) gave 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-phenylpyrimidin-2-yl)aniline as a white solid (450 mg).

Workup

  1. customThe reaction mixtures
  2. washwashed with H2O
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto give an orange oil

Sources & evidence

ORD record
ord-2cf194062a10475dab3910f7448ed57f
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Reaction notes

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