Ammonia → (S)-2-(1-((5-(2,4-Di hydroxyphenyl)-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 1052713Notes

Reaction equation

C[O:2][C:3]1[CH:8]=[C:7]([O:9]C)[CH:6]=[CH:5][C:4]=1[C:11]1[C:19]2[C:18]([NH:20][C@H:21]([C:23]3[N:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:27](=[O:35])[C:26]4=[C:36]([CH3:39])[CH:37]=[CH:38][N:25]4[N:24]=3)[CH3:22])=[N:17][CH:16]=[N:15][C:14]=2[N:13](COCC[Si](C)(C)C)[CH:12]=1.B(Br)(Br)Br.N>>[OH:2][C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:4]=1[C:11]1[C:19]2[C:18]([NH:20][C@H:21]([C:23]3[N:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:27](=[O:35])[C:26]4=[C:36]([CH3:39])[CH:37]=[CH:38][N:25]4[N:24]=3)[CH3:22])=[N:17][CH:16]=[N:15][C:14]=2[NH:13][CH:12]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 25134Boron tribromide

HCID 131736121(S)-2-(1-((5-(2,4-Dimethoxyphenyl)-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 73775930(S)-2-(1-((5-(2,4-Di hydroxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 21.7%

Procedure

(S)-2-(1-((5-(2,4-Dimethoxyphenyl)-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 (95 mg, 0.14 mmol) was treated with boron tribromide (1M in dichloromethane, 1.46 mL, 14.6 mmol) and a solution of ammonia (7N in methanol, 1.96 mL, 13.72 mmol) according to the method described in Example 41 to give 15 mg (21% yield) of the title compound. Purity 100%.

Sources & evidence

ORD record: ord-39a3e957bdff449794a2b9e0e50e3a3d
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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