Cesium fluoride → HCID 118433799, compound

HRID 1052507Notes

Reaction equation

HRID 1052507 reaction equation
[NH2:1][CH2:2][C:3]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:7](=[O:15])[C:6]2=[C:16]([CH3:19])[CH:17]=[CH:18][N:5]2[N:4]=1.[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][CH2:2][C:3]2[N:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:7](=[O:15])[C:6]3=[C:16]([CH3:19])[CH:17]=[CH:18][N:5]3[N:4]=2)[C:21]=1[Br:20]

Participants

5

Reactant 4

HCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 457897135-Bromo-6-chloropyrimidin-4-amineHCID 90103185HCID 90103185, compound

Product 1

HCID 118433799HCID 118433799, compoundYield 95%

Procedure

2-(Aminomethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (420 mg, 0.97 mmol) was treated with 5-bromo-6-chloropyrimidin-4-amine (304 mg, 1.46 mmol), cesium fluoride (222 mg, 1.46 mmol) and N,N-diisopropylethylamine (0.508 mL, 2.92 mol) according to Preparation 13. The residue was purified using SP1® Purification System (0% to 10%, dichloromethane-methanol) to give 394 m g (95% yield) of the title compound as a solid. Purity 100%.

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-b4b0f2fcc7134b838fafcea593f4c94e
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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