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

HRID 1052675Notes

Reaction equation

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

Participants

Reactant 3

HCID 222Ammonia

HCID 6422Trifluoroacetic acid

HCID 131736133(S)-2-(1-((5-(2-Hydroxyphenyl)-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 737766502-[(1S)-1-[[5-(2-hydroxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]amino]ethyl]-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4-oneYield 56%

Procedure

(S)-2-(1-((5-(2-Hydroxyphenyl)-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 (52 mg, 0.09 mmol) was treated with trifluoroacetic acid (1.04 mL, 13.50 mmol) and a solution of ammonia (7N in methanol, 1.04 mL, 7.28 mmol) according to the method described in Example 27 to give 23 mg (56% yield) of the title compound. Purity 98%.

Sources & evidence

ORD record: ord-4d55fc6728a447ca980438a8488f31af
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

Loading…