Sodium Carbonate → HCID 118483128, compound

HRID 1773358Notes

Reaction equation

HRID 1773358 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]([CH3:24])[C:16](=[O:23])[C:17](Cl)=[C:18]([C:20]#[N:21])[N:19]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[F:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][C:32]=1[O:33][CH3:34].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([O:5][C:6](=[O:25])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:15]([CH3:24])[C:16](=[O:23])[C:17]([C:29]3[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:27]([F:26])[CH:28]=3)=[C:18]([C:20]#[N:21])[N:19]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27821943-Fluoro-4-methoxyphenylboronic acidHCID 118483105HCID 118483105, compound

Product 1

HCID 118483128HCID 118483128, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of [1-(5-chloro-4-cyano-1-methyl-6-oxo-1,6-dihydro-pyrimidin-2-yl)-piperidin-4-yl]-carbamic acid tert-butyl ester (200 mg, 0.54 mmol), 3-fluoro-4-methoxybenzeneboronic acid (278 mg, 1.63 mmol), Pd(dppf)2Cl2 (119 mg, 0.16 mmol), and Na2CO3 (173 mg, 1.63 mmol) in dioxane (5 mL) and H2O (1 mL) was degassed with N2 and stirred at 145° C. in the microwave for 2 h. The reaction mixture was cooled to RT and filtered. The filtrate was concentrated in vacuo and the residue purified by preperative HPLC to give 110 mg of the desired product (45%). [M+H] Calc'd for C23H28FN5O4, 458. Found, 458.

Workup

  1. customwas degassed with N2
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue purified by preperative HPLC

Sources & evidence

ORD record
ord-27eaba2770024154b68a6058035b624c
Source dataset
uspto-grants-2016_02
Patent number
US09255097B2

Reaction notes

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