Cesium fluoride → HCID 118433965, compound

HRID 1052504Notes

Reaction equation

HRID 1052504 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].[Br:20][C:21]1[C:22]([NH2:28])=[N:23][CH:24]=[N:25][C:26]=1Cl.[F-].[Cs+].C(N(CC)C(C)C)(C)C>>[NH2:28][C:22]1[N:23]=[CH:24][N:25]=[C:26]([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])[C:21]=1[Br:20]

Participants

5

Reactant 4

HCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 457897135-Bromo-6-chloropyrimidin-4-amineHCID 118433975HCID 118433975, compound

Product 1

HCID 118433965HCID 118433965, compoundYield 71.1%

Procedure

(S)-2-(1-Aminoethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (1.2 g, 4.72 mmol) was treated 5-bromo-6-chloropyrimidin-4-amine (2 g, 9.6 mmol), cesium fluoride (1.44 g, 9.48 mmol), N,N-diisopropylethylamine (4.2 mL, 24.11 mol) according to Preparation 13. The residue was purified by flash chromatography using Isolera® Purification System (0% to 50%, dichloromethane-ethyl acetate) to give 1.43 g (71% yield) of the title compound as a solid. Purity 100%.

Workup

  1. customaccording to Preparation 13
  2. customThe residue was purified by flash chromatography
  3. customIsolera® Purification System (0% to 50%, dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-b1aa736b6e1a49a7bdddb467ed9e3d3d
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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