Ammonia → HCID 73775262, compound

HRID 1052703Notes

Reaction equation

HRID 1052703 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=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.B(Br)(Br)Br.N>>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=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

4

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 131736146HCID 131736146, compound

Product 1

HCID 73775262HCID 73775262, compoundYield 72%

Procedure

(S)-2-(1-((5-(2-Methoxy-5-methylphenyl)-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 (45 mg, 0.07 mmol) was treated with boron tribromide (1M in dichloromethane, 1.6 mL, 1.6 mmol) and a solution of ammonia (7N in methanol, 1.6 mL, 11.2 mmol) according to the method described in Example 41 to give 23.6 mg (72% yield) of the title. Purity 97%.

Workup

  1. customto give 23.6 mg (72% yield) of the title

Sources & evidence

ORD record
ord-367718e6239d48ddb1e9c2aed54cd4d7
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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