Cesium fluoride → (S)-2-(1-((5-Iodopyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052648Notes

Reaction equation

HRID 1052648 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=[CH:17][CH:18]=[CH:19][N:6]2[N:5]=1)[CH3:3].Cl[C:21]1[C:26]([I:27])=[CH:25][N:24]=[CH:23][N:22]=1.[F-].[Cs+].C(N(CC)C(C)C)(C)C>>[I:27][C:26]1[C:21]([NH:1][C@H:2]([C:4]2[N:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:8](=[O:16])[C:7]3=[CH:17][CH:18]=[CH:19][N:6]3[N:5]=2)[CH3:3])=[N:22][CH:23]=[N:24][CH:25]=1

Participants

5

Reactant 4

HCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 112302044-Chloro-5-iodopyrimidineHCID 118433975HCID 118433975, compound

Product 1

HCID 118433847(S)-2-(1-((5-Iodopyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 15.2%

Procedure

(S)-2-(1-Aminoethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (110 mg, 0.43 mmol) was treated with 4-chloro-5-iodopyrimidine (166 mg, 0.69 mmol), cesium fluoride (131 mg, 0.86 mmol) and N,N-diisopropylethylamine (377 μL, 2.16 mmol) according to Preparation 13. The residue was purified by reverse phase using SP1® Purification System to give 30 mg (13% yield) of the title compound as a solid. Purity 86%.

Workup

  1. customaccording to Preparation 13
  2. customThe residue was purified by reverse phase
  3. custom® Purification System

Sources & evidence

ORD record
ord-15924943c1e14e29b3fa5a88f5948884
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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