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

HRID 1052379Notes

Reaction equation

HRID 1052379 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:27]([I:28])=[CH:26][N:25]=[CH:24][N:23]=1.[F-].[Cs+].C(N(CC)C(C)C)(C)C>>[I:28][C:27]1[C:22]([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=[C:17]([CH3:20])[CH:18]=[CH:19][N:6]3[N:5]=2)[CH3:3])=[N:23][CH:24]=[N:25][CH:26]=1

Participants

5

Reactant 4

HCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 112302044-Chloro-5-iodopyrimidineHCID 90102580(S)-2-(1-Aminoethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 118433754(S)-2-(1-((5-Iodopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 33%

Procedure

(S)-2-(1-Aminoethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (400 mg, 1.49 mmol) was treated 4-chloro-5-iodopyrimidine (538 mg, 2.24 mmol), cesium fluoride (453 mg, 2.98 mmol) and N,N-diisopropylethylamine (1.3 mL, 7.46 mol) according to Preparation 13. The residue was purified by reverse phase using SP1® Purification System to give 230 mg (33% yield) of the title compound as a solid. Purity 100%.

Workup

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

Sources & evidence

ORD record
ord-1b38fb376ba14229bdb853aad8e111ac
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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