Potassium Carbonate → HCID 73776508, compound

HRID 1052690Notes

Reaction equation

HRID 1052690 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1I.[SH:29][C:30]1[CH:31]=[C:32]([OH:36])[CH:33]=[CH:34][CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.[Cu]I>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1[S:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([OH:36])[CH:31]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27366133-HydroxybenzenethiolHCID 118433756(S)-2-(1-((6-Amino-5-iodopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 73776508HCID 73776508, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6344DichloromethaneSolvent

Procedure

(S)-2-(1-((6-Amino-5-iodopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (100 mg, 0.21 mmol) was treated with 3-mercaptophenol (39 mg, 0.31 mmol), potassium carbonate (128 mg, 0.93 mmol) and copper(I) iodide (59 mg, 0.31 mmol) in a microwave vessel with dichloromethane as a solvent according to the method described in Preparation 44. The residue was purified using SP1® Purification System (0% to 100%, hexane-ethyl acetate) to give 30 mg (30% yield) of the title compound.

Workup

  1. customdescribed in Preparation 44
  2. customThe residue was purified
  3. customSP1® Purification System (0% to 100%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-fb034747e5b94875b09645158ccb2aa4
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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