Pyridine → (S)-2-(1-((5-(1-(3-Methoxyphenyl)-1H-pyrazol-3-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052625Notes

Reaction equation

HRID 1052625 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:14]3[C:13]([NH:15][C@H:16]([C:18]4[N:23]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[C:22](=[O:30])[C:21]5=[C:31]([CH3:34])[CH:32]=[CH:33][N:20]5[N:19]=4)[CH3:17])=[N:12][CH:11]=[N:10][C:9]=3[N:8]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[CH:7]=2)=[N:2]1.[CH3:43][O:44][C:45]1[CH:46]=[C:47](B(O)O)[CH:48]=[CH:49][CH:50]=1.N1C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:43][O:44][C:45]1[CH:50]=[C:49]([N:1]2[CH:5]=[CH:4][C:3]([C:6]3[C:14]4[C:13]([NH:15][C@H:16]([C:18]5[N:23]([C:24]6[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=6)[C:22](=[O:30])[C:21]6=[C:31]([CH3:34])[CH:32]=[CH:33][N:20]6[N:19]=5)[CH3:17])=[N:12][CH:11]=[N:10][C:9]=4[N:8]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:40])([CH3:42])[CH3:41])[CH:7]=3)=[N:2]2)[CH:48]=[CH:47][CH:46]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 178428095HCID 178428095, compound

Product 1

HCID 131736240(S)-2-(1-((5-(1-(3-Methoxyphenyl)-1H-pyrazol-3-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 9%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

(S)-2-(1-((5-(1H-Pyrazol-3-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (88 mg, 0.15 mmol) was dissolved in N,N-dimethylformamide (1.5 ml). (3-Methoxyphenyl)boronic acid (46 mg, 0.30 mmol), copper(II) acetate (4 mg, 0.02 mmol) and pyridine (28 μL, 0.34 mmol) were added and the mixture was stirred at 75° C. during 96 h. The reaction was poured into ice-water mixture, basified to pH 10 with sodium carbonate and extracted twice with ethyl acetate. The organics were combined and washed with water, brine, dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified using SP1® Purification System (0% to 50%, hexane-ethyl acetate) to give 9 mg (9% yield) of the title compound.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washwashed with water, brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified
  7. customSP1® Purification System (0% to 50%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-255ecc6891f24aa4808bc10f2d2c983d
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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