Cesium carbonate → HCID 90102619, compound

HRID 1052844Notes

Reaction equation

HRID 1052844 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1Br.[O:29]1[CH2:34][CH2:33][N:32]([S:35]([C:38]2[CH:39]=[C:40](B(O)O)[CH:41]=[CH:42][CH:43]=2)(=[O:37])=[O:36])[CH2:31][CH2:30]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1[C:40]1[CH:41]=[CH:42][CH:43]=[C:38]([S:35]([N:32]2[CH2:33][CH2:34][O:29][CH2:30][CH2:31]2)(=[O:37])=[O:36])[CH:39]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 44119633[3-(Morpholine-4-sulfonyl)phenyl]boronic acidHCID 118433733HCID 118433733, compound

Product 1

HCID 90102619HCID 90102619, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (S)-2-(1-((6-amino-5-bromopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (60 mg, 0.13 mmol) were added (3-(morpholinosulfonyl)phenyl)boronic acid (54 mg, 0.2 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (11 mg, 0.01 mmol) and 133 μl of a 2M aqueous solution of cesium carbonate in dioxane (2 ml). The mixture was stirred under argon atmosphere at 100° C. for 18 hours and then diluted with ethyl acetate. The resulting solution was washed with water and brine, dried over magnesium sulphate, filtered and the solvents were removed under reduced pressure. The crude was purified using SP1® Purification System (50 to 100%, hexane-ethyl acetate) to give 58 mg (73% yield) of the title compound as a white solid. Purity 100%.

Workup

  1. washThe resulting solution was washed with water and brine
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customThe crude was purified
  6. customSP1® Purification System (50 to 100%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-d0b199d01c10408fa300b7874b79f211
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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