Potassium Carbonate → HCID 25182018, compound

HRID 2037400Notes

Reaction equation

HRID 2037400 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:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[F:22][C:23]1[CH:28]=[CH:27][C:26]([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:25][CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 58109314HCID 58109314, compound

Product 1

HCID 25182018HCID 25182018, compoundYield 25%

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 (50 mg, 0.165 mmol) and 4-fluorophenylboronic acid (32 mg, 0.33 mmol), K2CO3 (0.5 mL, 2 M) in 1,4-dioxane (1.5 ml) at 0° C. under N2 was slowly added Pd(Ph3)2Cl2 (10 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-(4-fluorophenyl)pyrimidin-4-yl)-6-methyl-6-phenyl-1,3-oxazinan-2-one (15 mg, yield 25%). 1H NMR (CDCl3, 400 MHZ): δ=1.75 (s, 3H), 2.4 (m, 1H), 2.54 (m, 1H), 3.6 (m, 1H), 4.4 (m, 1H), 7.1 (m, 2H), 7.25-7.4 (m, 5H), 8.08 (m, 1H), 8.34 (m, 2H), 8.62 (m, 1H). LC-MS Method 3, tR=1.519 min, m/z=364.1. 1H NMR (CDCl3) 1.80 (s, 3H), 2.40 (m, 1H), 2.60-2.70 (d, 1H), 3.60 (m, 1H), 4.40 (t, 1H), 7.10 (t, 2H), 7.20-7.45 (m, 5H), 8.17 (d, 1H), 8.35 (t, 2H), 8.65 (d, 1H).

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-8c70ccfaee8c4edebeb8a5a94af5a272
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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