Potassium Carbonate → HCID 25182017, compound

HRID 2037401Notes

Reaction equation

HRID 2037401 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][C:11]([CH3:20])([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:10][C:9]2=[O:21])[CH:5]=[CH:4][N:3]=1.[F:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[F:22][C:23]1[CH:28]=[C:27]([C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][C:11]([CH3:20])([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[O:10][C:9]3=[O:21])[CH:5]=[CH:4][N:3]=2)[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 58109314HCID 58109314, compound

Product 1

HCID 25182017HCID 25182017, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-(2-chloropyrimidin-4-yl)-6-methyl-6-phenyl-1,3-oxazinan-2-one (100 mg, 0.33 mmol) and 3-fluorophenylboronic acid (80 mg, 0.53 mmol), K2CO3 (1 mL, 2 M) in 1,4-dioxane (3 ml) at 0° C. under N2 was slowly added Pd(Ph3)2Cl2 (20 mg, 20%). The mixture was refluxed overnight. The mixture was concentrated to give the crude product, which was purified by TLC and preparative HPLC to afford 3-(2-(3-fluorophenyl)pyrimidin-4-yl)-6-methyl-6-phenyl-1,3-oxazinan-2-one (20 mg, yield 17%). 1H NMR (CDCl3, 400 MHZ): δ=1.71 (s, 3H), 2.37 (m, 1H), 2.6 (m, 1H), 3.54 (m, 1H), 4.34 (m, 1H), 7.08 (m, 1H), 7.25 (m, 1H), 7.34 (m, 5H), 7.96 (m, 1H), 8.09 (m, 1H), 8.16 (m, 1H), 8.6 (m, 1H). LC-MS Method 3, tR=1.46 min, m/z=364.

Workup

  1. customat 0° C.
  2. temperatureThe mixture was refluxed overnight
  3. concentrationThe mixture was concentrated
  4. customto give the crude product, which
  5. customwas purified by TLC and preparative HPLC

Sources & evidence

ORD record
ord-bd2bf5956bcc4c5d9dc49c93e60c9c22
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…