Water → HCID 70651396, compound

HRID 1426034Notes

Reaction equation

HRID 1426034 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:12][CH2:11][N:10]([CH3:13])[C:9]2=[O:14])=[N:6][CH:7]=1.[OH:15][C:16]([CH3:49])([CH3:48])[CH2:17][C@@:18]1([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[O:23][C:22](=[O:24])[N:21]([C@H:25]([C:27]2[CH:32]=[CH:31][C:30](B3OC(C)(C)C(C)(C)O3)=[CH:29][CH:28]=2)[CH3:26])[CH2:20][CH2:19]1.C([O-])([O-])=O.[Na+].[Na+].O>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:15][C:16]([CH3:48])([CH3:49])[CH2:17][C@@:18]1([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[O:23][C:22](=[O:24])[N:21]([C@H:25]([C:27]2[CH:28]=[CH:29][C:30]([C:2]3[CH:3]=[N:4][C:5]([N:8]4[CH2:12][CH2:11][N:10]([CH3:13])[C:9]4=[O:14])=[N:6][CH:7]=3)=[CH:31][CH:32]=2)[CH3:26])[CH2:20][CH2:19]1

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 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-oneHCID 67998151HCID 67998151, compound

Product 1

HCID 70651396HCID 70651396, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Pd(PPh3)4 (1 mg) was added to a solution of 1-(5-bromopyrimidin-2-yl)-3-methylimidazolidin-2-one (10 mg), (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 (38.0 mg), and Na2CO3 (17 mg) in toluene (3 mL), ethanol (2 mL), and H2O (1 mL) under nitrogen at room temperature. The reaction mixture was heated to 100° C. under nitrogen and stirred at this temperature for 2 h. After cooling to room temperature, the mixture was concentrated to afford an oil, which was purified by preparative HPLC to give the title compound. Yield: 2.4 mg (12% of theory); LC (method 4): tR=0.98 min; Mass spectrum (ESI+): m/z=530 [M+H]+; 1H NMR (CD3OD) δ 0.88 (s, 3H), 1.32 (s, 3H), 1.48 (d, 3H), 2.05 (m, 2H), 2.12 (m, 2H), 2.41 (m, 2H), 2.81 (s, 3H), 3.42 (m, 2H), 4.01 (m, 2H), 5.52 (m, 1H), 7.02 (d, 2H), 7.26 (m, 5H), 7.31 (m, 2H), 8.67 (s, 2H).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated
  3. customto afford an oil, which
  4. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-f1c82697c32945379c849d7d7103a6cd
Source dataset
uspto-grants-2015_01
Patent number
US08933072B2

Reaction notes

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