Diisopropylethylamine → (S)-2-(1-((6-Bromothieno[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052418Notes

Reaction equation

HRID 1052418 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[S:31][C:25]2[N:26]=[CH:27][N:28]=[C:29](Cl)[C:24]=2[CH:23]=1.C(N(CC)C(C)C)(C)C>C(O)(C)(C)C>[Br:21][C:22]1[S:31][C:25]2[N:26]=[CH:27][N:28]=[C:29]([NH:1][C@H:2]([C:4]3[N:9]([C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:8](=[O:16])[C:7]4=[C:17]([CH3:20])[CH:18]=[CH:19][N:6]4[N:5]=3)[CH3:3])[C:24]=2[CH:23]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 122252616-Bromo-4-chlorothieno[2,3-d]pyrimidineHCID 90102580(S)-2-(1-Aminoethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 118433746(S)-2-(1-((6-Bromothieno[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 42.7%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

(S)-2-(1-Aminoethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (219 mg, 0.72 mmol) was treated with 6-bromo-4-chlorothieno[2,3-d]pyrimidine (179 mg, 0.72 mmol), N,N-diisopropylethylamine (751 μl, 4.31 mmol) and tert-butanol as a solvent according to the method described in Example 17. The crude was purified using SP1® Purification (0% to 30%, hexane-ethyl acetate) to give 148 mg (42% yield) of the title compound as a white solid. Purity 97%.

Workup

  1. customThe crude was purified
  2. custom® Purification (0% to 30%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1a0a69d893044f458ce71b542ed75754
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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