Cesium fluoride → HCID 118433733, compound

HRID 1052376Notes

Reaction equation

HRID 1052376 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].[Br:21][C:22]1[C:23]([NH2:29])=[N:24][CH:25]=[N:26][C:27]=1Cl.[F-].[Cs+].C(N(CC)C(C)C)(C)C>>[NH2:29][C:23]1[N:24]=[CH:25][N:26]=[C:27]([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])[C:22]=1[Br:21]

Participants

5

Reactant 4

HCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 457897135-Bromo-6-chloropyrimidin-4-amineHCID 90102580(S)-2-(1-Aminoethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 118433733HCID 118433733, compoundYield 60%

Procedure

(S)-2-(1-Aminoethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (300 mg, 1.12 mmol) was treated 5-bromo-6-chloropyrimidin-4-amine (373 mg, 1.79 mmol), cesium fluoride (340 mg, 2.24 mmol), N,N-diisopropylethylamine (0.974 mL, 5.59 mol) according to Preparation 13. The residue was purified using SP1® Purification System (0% to 10%, dichloromethane-methanol) to give 0.26 g (60% yield) of the title compound as a solid. Purity 98%.

Workup

  1. customaccording to Preparation 13
  2. customThe residue was purified
  3. customSP1® Purification System (0% to 10%, dichloromethane-methanol)

Sources & evidence

ORD record
ord-c633e83640484fcdad3cd41e179e88b1
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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