Potassium Carbonate → HCID 66576812, compound

HRID 523600Notes

Reaction equation

HRID 523600 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:12][CH2:11][N:10]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][C:18]=3[CH:19]3[CH2:21][CH2:20]3)[C:9]2=[O:22])[CH:3]=1.[CH:23]1(B(O)O)[CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+]>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.C1(C)C(C)=CC=CC=1>[CH:19]1([C:18]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N:10]2[CH2:11][CH2:12][N:8]([C:4]3[CH:3]=[C:2]([CH:23]4[CH2:25][CH2:24]4)[N:7]=[CH:6][N:5]=3)[C:9]2=[O:22])[CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2760897Cyclopropylboronic acidHCID 66576563HCID 66576563, compound

Product 1

HCID 66576812HCID 66576812, compoundYield 38.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 7237O-XyleneSolvent

Procedure

Using analogous reagents and reaction conditions as described in Example 1 above, 1-(6-chloropyrimidin-4-yl)-3-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one (I-38a: 140 mg, 0.44 mmol) was reacted with cyclopropyl boronic acid (46 mg, 0.533 mmol), Pd(PPh3)4 (26 mg, 0.02 mmol), potassium carbonate (123 mg, 0.888 mmol) and xylene (10 mL) in seal tube at 125° C. for 14 hours. Purification by column chromatography on silica gel (1% methanol in chloroform) afforded 55 mg of the product (38.73% yield).

Workup

  1. customreagents and reaction conditions
  2. customPurification by column chromatography on silica gel (1% methanol in chloroform)

Sources & evidence

ORD record
ord-6197d5bd51504321b95bc881078e626f
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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