Potassium Carbonate → HCID 68290770, compound

HRID 538243Notes

Reaction equation

HRID 538243 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[C:12](I)[C:11]3=[N:15][C:16]([CH2:18][O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:17][N:10]3[C:9]2=[O:26])=[CH:4][CH:3]=1.[CH3:27]B(O)O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CN(C=O)C.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>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[C:12]([CH3:27])[C:11]3=[N:15][C:16]([CH2:18][O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:17][N:10]3[C:9]2=[O:26])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 139377Methylboronic AcidHCID 68290931HCID 68290931, compound

Product 1

HCID 68290770HCID 68290770, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (2.63 mg, 0.0023 mmol) was added to a stirred suspension of 6-(4-fluoro-phenyl)-8-iodo-2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one (35 mg, 0.076 mmol), methylboronic acid (22.7 mg, 0.38 mmol) and K2CO3 (31.5 mg, 0.23 mmol) in a mixture of 1,4-dioxane (4 mL) and DMF (1 mL) under nitrogen and in a sealed tube. The mixture was stirred at 150° C. for 45 minutes under microwave irradiation. The solvents were evaporated in vacuo and the crude product was purified by flash column chromatography (silica; AcOEt in DCM with a gradient of 0/100 to 20/80). The desired fractions were collected and the solvents evaporated in vacuo to yield 6-(4-fluoro-phenyl)-8-methyl-2-phenoxymethyl-6H-imidazo[1,2-c]pyrimidin-5-one (19 mg, 72% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ ppm 2.36 (d, J=1.2 Hz, 3H), 5.22 (s, 2H), 6.92 (d, J=1.2 Hz, 1H), 6.97 (br. t, J=7.4, 7.4 Hz, 1H), 7.02 (br. d, J=8.1 Hz, 2H), 7.16-7.24 (m, 2H), 7.27-7.34 (m, 2H), 7.36-7.44 (m, 2H), 7.84 (s, 1H).

Workup

  1. customThe solvents were evaporated in vacuo
  2. customthe crude product was purified by flash column chromatography (silica
  3. customThe desired fractions were collected
  4. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-cd2958ddb98a4e60a72a973bf142a61b
Source dataset
uspto-grants-2014_10
Patent number
US08865725B2

Reaction notes

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