Cesium fluoride → (S)-2-(1-((5-((3-Methoxyphenyl)thio)-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 1052422Notes

Reaction equation

HRID 1052422 reaction equation
[NH2:1][C@H:2]([C:4]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8](=[O:16])[C:7]2=[C:17]([CH3:20])[CH:18]=[CH:19][N:6]2[N:5]=1)[CH3:3].Cl[C:22]1[C:23]2[C:30]([S:31][C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([O:38][CH3:39])[CH:33]=3)=[CH:29][N:28]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:47])([CH3:46])[CH3:45])[C:24]=2[N:25]=[CH:26][N:27]=1.C(N(CC)C(C)C)(C)C.[F-].[Cs+]>C(O)(C)(C)C>[CH3:39][O:38][C:34]1[CH:33]=[C:32]([S:31][C:30]2[C:23]3[C:22]([NH:1][C@H:2]([C:4]4[N:9]([C:10]5[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=5)[C:8](=[O:16])[C:7]5=[C:17]([CH3:20])[CH:18]=[CH:19][N:6]5[N:5]=4)[CH3:3])=[N:27][CH:26]=[N:25][C:24]=3[N:28]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:45])([CH3:47])[CH3:46])[CH:29]=2)[CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 90102580(S)-2-(1-Aminoethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneHCID 90103343HCID 90103343, compound

Product 1

HCID 131736150(S)-2-(1-((5-((3-Methoxyphenyl)thio)-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 35.5%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

(S)-2-(1-Aminoethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (60 mg, 0.22 mmol) was treated with 4-chloro-5-((3-methoxyphenyl)thio)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (109 mg, 0.26 mmol), N,N-diisopropylethylamine (195 μl, 1.12 mmol), cesium fluoride (41 mg, 0.27 mmol) and tert-butanol as a solvent according to the method described in Example 17. The crude was purified using SP1® Purification (0% to 50%, hexane-ethyl acetate) to give 51 mg (35% yield) of the title compound as a white solid. Purity 100%.

Workup

  1. customThe crude was purified
  2. custom® Purification (0% to 50%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-ee708ceb933d480db1aedd58bc7ec93c
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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