Cesium fluoride → HCID 118433835, compound

HRID 1052384Notes

Reaction equation

HRID 1052384 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]([S:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:18]=[CH:19][N:6]2[N:5]=1)[CH3:3].[Br:27][C:28]1[C:29]([NH2:35])=[N:30][CH:31]=[N:32][C:33]=1Cl.[F-].[Cs+].C(N(CC)C(C)C)(C)C>>[NH2:35][C:29]1[N:30]=[CH:31][N:32]=[C:33]([NH:1][C@H:2]([C:4]2[N:9]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:8](=[O:16])[C:7]3=[C:17]([S:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:18]=[CH:19][N:6]3[N:5]=2)[CH3:3])[C:28]=1[Br:27]

Participants

5

Reactant 4

HCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 457897135-Bromo-6-chloropyrimidin-4-amineHCID 118433752HCID 118433752, compound

Product 1

HCID 118433835HCID 118433835, compoundYield 110.3%

Procedure

(S)-2-(1-Aminoethyl)-3-phenyl-5-(phenylthio)pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (142 mg, 0.39 mmol) was treated with treated 5-bromo-6-chloropyrimidin-4-amine (245 mg, 1.18 mmol), cesium fluoride (178 mg, 1.17 mmol), N,N-diisopropylethylamine (341 μl, 1.96 mol) according to Preparation 13 to give 0.23 g (75% yield) of the title compound as a solid.

Workup

  1. customaccording to Preparation 13

Sources & evidence

ORD record
ord-0e75391018d84ccc9ecb7fbcc2fee05e
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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