Cesium carbonate → HCID 73776367, compound

HRID 1052743Notes

Reaction equation

HRID 1052743 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.[OH:29][C:30]1[CH:55]=[CH:54][C:33]([C:34]([NH:36][C:37]2[C:38]([O:52][CH3:53])=[N:39][CH:40]=[C:41](B3OC(C)(C)C(C)(C)O3)[CH:42]=2)=[O:35])=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]([C:41]2[CH:42]=[C:37]([NH:36][C:34](=[O:35])[C:33]3[CH:32]=[CH:31][C:30]([OH:29])=[CH:55][CH:54]=3)[C:38]([O:52][CH3:53])=[N:39][CH:40]=2)=[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])[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 90103271HCID 90103271, compoundHCID 118433733HCID 118433733, compound

Product 1

HCID 73776367HCID 73776367, compoundYield 22%

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 (84 mg, 0.19 mmol) were added 4-hydroxy-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzamide (85 mg, 0.23 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (16 mg, 0.02 mmol) and 191 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 (0 to 65%, hexane-ethyl acetate) to give 25 mg (22% 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 (0 to 65%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-37b1af72b95442178c70eb424fed4dfd
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

Loading…