Sodium Carbonate → HCID 58109240, compound

HRID 2037754Notes

Reaction equation

HRID 2037754 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[OH:7][C:8]([CH3:41])([CH3:40])[CH2:9][C@@:10]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:15][C:14](=[O:16])[N:13]([C@H:17]([C:19]2[CH:24]=[CH:23][C:22](B3OC(C)(C)C(C)(C)O3)=[CH:21][CH:20]=2)[CH3:18])[CH2:12][CH2:11]1.BrC1C=NC(C[CH:50]2[C:55](Br)=[CH:54][NH:53][C:52]([CH3:57])=[N:51]2)=NC=1>CN(C)C=O>[OH:7][C:8]([CH3:40])([CH3:41])[CH2:9][C@@:10]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:15][C:14](=[O:16])[N:13]([C@H:17]([C:19]2[CH:20]=[CH:21][C:22]([C:55]3[CH:54]=[N:53][C:52]([CH3:57])=[N:51][CH:50]=3)=[CH:23][CH:24]=2)[CH3:18])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 58109374HCID 58109374, compoundHCID 59532385(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-((S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl)-1,3-oxazinan-2-one

Product 1

HCID 58109240HCID 58109240, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2 M aqueous Na2CO3 solution (1.67 mL) was added to a solution of (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-[(S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethyl]-1,3-oxazinan-2-one (0.80 g) and 5-bromo-2-(5-bromo-2-methyl-1,4-dihydro-pyrimidin-4-ylmethyl)-pyrimidine (0.40 g) in dimethylformamide (5 mL). The resulting mixture was sparged with argon for 5 min, before [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) dichloromethane complex (82 mg) was added. The mixture was heated to 100° C. and stirred at this temperature overnight. After cooling to ambient temperature, water was added, and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), and concentrated. The residue was purified by chromatography on silica gel (CH2Cl2/MeOH 95:5→80:20) followed by HPLC (MeCN/H2O/NH4OH) to afford the title compound (340 mg) which was crystallized from iPr2O. Yield: 0.25 g (34% of theory). Mass spectrum (ESI+): m/z=446 [M+H]+

Workup

  1. customThe resulting mixture was sparged with argon for 5 min, before [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) dichloromethane complex (82 mg)
  2. additionwas added
  3. temperatureAfter cooling to ambient temperature
  4. additionwater was added
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe residue was purified by chromatography on silica gel (CH2Cl2/MeOH 95:5→80:20)

Sources & evidence

ORD record
ord-f97ace49558e4178b40382a8258d5567
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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