Ethanol → HCID 18669678, compound

HRID 1059002Notes

Reaction equation

HRID 1059002 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)[CH:16]=3)[CH2:13][CH2:12][C:11](=[O:14])[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.[NH2:29][C:30]1[N:35]=[CH:34][C:33](B2OC(C)(C)C(C)(C)O2)=[CH:32][N:31]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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.O>[NH2:29][C:30]1[N:31]=[CH:32][C:33]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3([C:15]4[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH:24]5[CH2:25][CH2:26][CH2:27][CH2:28]5)[CH:16]=4)[CH2:13][CH2:12][C:11](=[O:14])[CH:10]=[CH:9]3)=[CH:4][CH:3]=2)=[CH:34][N:35]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 23563768HCID 23563768, compound

Product 1

HCID 18669678HCID 18669678, compoundYield 83.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(4-bromophenyl)-4-(3-cyclopentyloxy-4-methoxyphenyl)-2-cylohexen-1-one (1.39 g, 3.17 mmol) in Toluene (50 ml) was added tetrakis(triphenylphosphine)palladium(0) (417 mg, 0.36 mmol), followed by 2-(2-aminopyrimidin-5-yl)-4,4,5,5-tetramethyl-1,3-dioxaborolane (2.02 g, 6.1 mmol, prepared as described in Tatsuo Ishiyama; Miki Murata and Norio Miyaura, J. Org. Chem. 1995, 60, 7508-7510), ethanol (8 ml) and 2M sodium carbonate (8 ml). The reaction mixture was stirred under argon at 80° C. for 18 h. Water was added and the mixture extracted three times with ethyl acetate, the combined organic extract was washed with water then brine, dried (sodium sulfate) and evaporated. Purification by flash chromatography (silica gel, 73% ethyl acetate/27% hexane) provided the title compound as a white solid (1.2 g, 83% crude yield). MS (m/e): 456 [(M+1)+].

Workup

  1. extractionthe mixture extracted three times with ethyl acetate
  2. extractionthe combined organic extract
  3. washwas washed with water
  4. dry with materialbrine, dried (sodium sulfate)
  5. customevaporated
  6. customPurification by flash chromatography (silica gel, 73% ethyl acetate/27% hexane)

Sources & evidence

ORD record
ord-2a320067821d465b87f6f2598d8099bd
Source dataset
uspto-grants-2003_02
Patent number
US06518306B1

Reaction notes

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