Ammonia → (S)-2-(1-((5-(6-Methoxypyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052696Notes

Reaction equation

HRID 1052696 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[C:17]3[C:16]([NH:18][C@H:19]([C:21]4[N:26]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[C:25](=[O:33])[C:24]5=[C:34]([CH3:37])[CH:35]=[CH:36][N:23]5[N:22]=4)[CH3:20])=[N:15][CH:14]=[N:13][C:12]=3[N:11](COCC[Si](C)(C)C)[CH:10]=2)[CH:6]=[CH:5][CH:4]=1.FC(F)(F)C(O)=O.N>CO>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[C:17]3[C:16]([NH:18][C@H:19]([C:21]4[N:26]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[C:25](=[O:33])[C:24]5=[C:34]([CH3:37])[CH:35]=[CH:36][N:23]5[N:22]=4)[CH3:20])=[N:15][CH:14]=[N:13][C:12]=3[NH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 131736145HCID 131736145, compound

Product 1

HCID 73776365(S)-2-(1-((5-(6-Methoxypyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-2-(1-((5-(6-Methoxypyridin-2-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (17 mg, 0.02 mmol) was treated with trifluoroacetic acid (340 μl, 4.41 mmol), a solution of ammonia (7N in methanol, 340 μl, 2.38 mmol) in 370 μl methanol according to the method described in Example 27 to give 5 mg (59% yield) of the title compound. Purity 100%.

Sources & evidence

ORD record
ord-f2c62cb140be4dfbb5ef85ff39106422
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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