Ammonia → (S)-2-(1-((5-(3-Hydroxybenzyl)-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 1052689Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]([CH:44]=[CH:45][CH:46]=1)[CH2:6][C:7]1[C:15]2[C:14]([NH:16][C@H:17]([C:19]3[N:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:23](=[O:31])[C:22]4=[C:32]([CH3:35])[CH:33]=[CH:34][N:21]4[N:20]=3)[CH3:18])=[N:13][CH:12]=[N:11][C:10]=2[N:9](COCC[Si](C)(C)C)[CH:8]=1.B(Br)(Br)Br.N>>[OH:2][C:3]1[CH:4]=[C:5]([CH:44]=[CH:45][CH:46]=1)[CH2:6][C:7]1[C:15]2[C:14]([NH:16][C@H:17]([C:19]3[N:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:23](=[O:31])[C:22]4=[C:32]([CH3:35])[CH:33]=[CH:34][N:21]4[N:20]=3)[CH3:18])=[N:13][CH:12]=[N:11][C:10]=2[NH:9][CH:8]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 25134Boron tribromide

HCID 131736139(S)-2-(1-((5-(3-Methoxybenzyl)-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 73776511(S)-2-(1-((5-(3-Hydroxybenzyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 81.4%

Procedure

(S)-2-(1-((5-(3-Methoxybenzyl)-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 (55 mg, 0.04 mmol) was treated with boron tribromide (1M in dichloromethane, 1.7 mL, 1.7 mmol) and a solution of ammonia (7N in methanol, 1 mL, 7 mmol) according to the method described in Example 41 to give 16 mg (75% yield) of the title compound as a white solid. Purity 100%.

Sources & evidence

ORD record: ord-ac56eb655d1a45d48be987239d49fd71
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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