Potassium Carbonate → HCID 118483097, compound

HRID 1773347Notes

Reaction equation

HRID 1773347 reaction equation
[CH3:1][O:2][C:3](=[O:36])[CH2:4][N:5]1[C:10](=[O:11])[C:9](Cl)=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[C:15]([F:21])[CH:14]=2)[N:7]=[C:6]1[N:22]1[CH2:27][CH2:26][CH:25]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24][CH2:23]1.[C:37]([O-:40])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:36])[CH2:4][N:5]1[C:10](=[O:11])[C:9]([C:13]2[CH:18]=[CH:17][C:16]([O:40][CH3:37])=[CH:15][CH:14]=2)=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[C:15]([F:21])[CH:14]=2)[N:7]=[C:6]1[N:22]1[CH2:27][CH2:26][CH:25]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24][CH2:23]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 118483144HCID 118483144, compound

Product 1

HCID 118483097HCID 118483097, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of [2-(4-tert-butoxycarbonylamino-piperidin-1-yl)-5-chloro-4-(4-cyano-3-fluoro-phenyl)-6-oxo-6H-pyrimidin-1-yl]-acetic acid methyl ester (2.2 g, 4.2 mmol), p-methoxyboronic acid (1.9 g, 12.7 mmol), Pd-118 (274 mg, 0.42 mmol) and K2CO3 (1.2 g, 8.4 mmol) in DMF (50 mL) was stirred at 145° C. for 6 h under nitrogen atmosphere. The reaction mixture was diluted with water and extracted with EA (3×). The combined organics were washed with water, washed brine, dried (Na2SO4) and concentrated. The residue was purified by preparative HPLC to give 600 mg of the title product (24%). [M+H] Calc'd for C31H34FN5O6, 592. Found, 592.

Workup

  1. extractionextracted with EA (3×)
  2. washThe combined organics were washed with water
  3. washwashed brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-ca9cf1db7d964572881d91a46e4d2a5b
Source dataset
uspto-grants-2016_02
Patent number
US09255097B2

Reaction notes

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