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

HRID 1052709Notes

Reaction equation

[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]1[C:18]2[C:17]([NH:19][C@H:20]([C:22]3[N:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:26](=[O:34])[C:25]4=[C:35]([CH3:38])[CH:36]=[CH:37][N:24]4[N:23]=3)[CH3:21])=[N:16][CH:15]=[N:14][C:13]=2[N:12](COCC[Si](C)(C)C)[CH:11]=1.FC(F)(F)C(O)=O.N>>[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]1[C:18]2[C:17]([NH:19][C@H:20]([C:22]3[N:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:26](=[O:34])[C:25]4=[C:35]([CH3:38])[CH:36]=[CH:37][N:24]4[N:23]=3)[CH3:21])=[N:16][CH:15]=[N:14][C:13]=2[NH:12][CH:11]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 6422Trifluoroacetic acid

HCID 131736149(S)-2-(1-((5-(2-Hydroxy-3-methoxyphenyl)-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

Product 1

HCID 737757982-[(1S)-1-[[5-(2-hydroxy-3-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amino]ethyl]-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4-oneYield 48%

Procedure

(S)-2-(1-((5-(2-Hydroxy-3-methoxyphenyl)-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 (71 mg, 0.08 mmol) was treated with trifluoroacetic acid (2 mL, 25.96 mmol) and a solution of ammonia (7N in methanol, 2 mL, 14 mmol) according to the method described in Example 27 to give 19.5 mg (48% yield) of the title compound. Purity 94%.

Sources & evidence

ORD record: ord-d6025b1c6bbd4a4e9b003736afb23a79
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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