Potassium Carbonate → HCID 73776062, compound

HRID 1052701Notes

Reaction equation

HRID 1052701 reaction equation
Br[C:2]1[S:34][C:5]2[N:6]=[C:7]([CH2:30][CH2:31][CH2:32][CH3:33])[N:8]=[C:9]([NH:10][C@H:11]([C:13]3[N:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:17](=[O:25])[C:16]4=[C:26]([CH3:29])[CH:27]=[CH:28][N:15]4[N:14]=3)[CH3:12])[C:4]=2[CH:3]=1.[C:35](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:30]([C:7]1[N:8]=[C:9]([NH:10][C@H:11]([C:13]2[N:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:17](=[O:25])[C:16]3=[C:26]([CH3:29])[CH:27]=[CH:28][N:15]3[N:14]=2)[CH3:12])[C:4]2[CH:3]=[C:2]([CH3:35])[S:34][C:5]=2[N:6]=1)[CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 118433967HCID 118433967, compound

Product 1

HCID 73776062HCID 73776062, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

(S)-2-(1-((6-Bromo-2-butylthieno[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (obtained as by-product in Preparation 82, 53 mg, 0.10 mmol) was treated with potassium carbonate (273 mg, 1.97 mmol), tetrakis(triphenylphosphine)palladium(0) (11 mg, 0.01 mmol) and trimethylboroxine (124 μl, 0.89 mmol) according to the method described in Example 56. The residue was purified using SP1® Purification System (0% to 35%, hexane-ethyl acetate) to obtain 17 mg (37% yield) of the title compound as a white solid. Purity 86%.

Workup

  1. customThe residue was purified
  2. customSP1® Purification System (0% to 35%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-de8b78f45fd54a1ab2b6366fdde09a22
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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