tert-Butanol → HCID 68195282, compound

HRID 2169645Notes

Reaction equation

HRID 2169645 reaction equation
Br[C:2]1[C:3]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH:15]2[C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)=[O:21])=[N:4][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[CH3:13])=[N:6][CH:7]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)(C)(C)C>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:13][C:9]1[N:8]([C:5]2[N:6]=[CH:7][C:2]3[N:22]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:31])=[O:32])=[CH:26][CH:25]=4)[C:20](=[O:21])[CH:15]4[CH2:16][O:17][CH2:18][CH2:19][N:14]4[C:3]=3[N:4]=2)[CH:12]=[CH:11][N:10]=1

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 68194860HCID 68194860, compound

Product 1

HCID 68195282HCID 68195282, compoundYield 63.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(5-bromo-2-(2-methyl-1H-imidazol-1-yl)pyrimidin-4-yl)-N-(4-(methylsulfonyl)benzyl)morpholine-3-carboxamide (100 mg, 0.187 mmol), palladium(II) acetate (4.19 mg, 0.019 mmol), Xantphos (21.61 mg, 0.037 mmol), and potassium phosphate, tribasic (79 mg, 0.374 mmol) in 1,4-dioxane (1 mL) and tert-butanol 0.25 mL was heated to 100° C. in a microwave for 1 hour and then heated again to 100° C. in the microwave for 10 hours. Water was subsequently added to the reaction mixture, which formed a precipitate that was collected by filtration. The solids were washed with water and EtOAc to afford the title compound as an off-white solid (54.2 mg, 63.8%). 1H NMR (400 MHz, DMSO-d6) δ 2.63 (s, 3 H), 3.02-3.13 (m, 1 H), 3.21 (s, 3 H), 3.53-3.64 (m, 1 H), 3.71 (t, J=10.99 Hz, 1 H), 3.98-4.06 (m, 1 H), 4.26 (dd, J=11.24, 3.92 Hz, 1 H), 4.37-4.45 (m, 1 H), 4.65 (dd, J=10.61, 3.79 Hz, 1 H), 5.17-5.37 (m, 2 H), 6.83 (d, J=1.52 Hz, 1 H), 7.59 (d, J=8.34 Hz, 2 H), 7.73 (d, J=1.52 Hz, 1 H), 7.84-7.94 (m, 3 H). ESI-MS m/z [M+H]+ calc'd for C21H22N6O4S, 455.14; found 455.3.

Workup

  1. customformed a precipitate that
  2. filtrationwas collected by filtration
  3. washThe solids were washed with water and EtOAc

Sources & evidence

ORD record
ord-604e311d39804c11a7164464d0f192a5
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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