Cesium fluoride → (S)-2-(1-((6-Amino-5-iodopyrimidin-4-yl)amino)ethyl)-5-bromo-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052341Notes

Reaction equation

HRID 1052341 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]([Br:20])[CH:18]=[CH:19][N:6]2[N:5]=1)[CH3:3].Cl[C:22]1[N:27]=[CH:26][N:25]=[C:24]([NH2:28])[C:23]=1[I:29].[F-].[Cs+].C(N(CC)C(C)C)(C)C>>[NH2:28][C:24]1[N:25]=[CH:26][N:27]=[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]([Br:20])[CH:18]=[CH:19][N:6]3[N:5]=2)[CH3:3])[C:23]=1[I:29]

Participants

5

Reactant 4

HCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 468558336-Chloro-5-iodopyrimidin-4-amineHCID 118433911(S)-2-(1-Aminoethyl)-5-bromo-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 118433900(S)-2-(1-((6-Amino-5-iodopyrimidin-4-yl)amino)ethyl)-5-bromo-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 32%

Procedure

(S)-2-(1-Aminoethyl)-5-bromo-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (0.72 g, 2.16 mol) was treated with 6-chloro-5-iodopyrimidin-4-amine (1.55 g, 4.31 mol), cesium fluoride (0.66 g, 4.34 mol), N,N-diisopropylethylamine (1.88 mL, 10.79 mol) according to Preparation 13. The residue was purified using SP1® Purification System (0% to 70%, hexane-ethyl acetate) to give 0.39 g (32% yield) of the title compound as a solid. Purity 93%.

Workup

  1. customaccording to Preparation 13
  2. customThe residue was purified
  3. customSP1® Purification System (0% to 70%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-36b8027db1584b0d9968ebb362475863
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

Loading…