Water → HCID 58009787, compound

HRID 1628057Notes

Reaction equation

HRID 1628057 reaction equation
[N:1]([CH2:4][C:5]1[N:6]=[C:7]2[CH:13]=[C:12]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=4)[N:16]([CH3:25])[CH:15]=3)[N:11]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[C:8]2=[N:9][CH:10]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH4+:1].[OH-:23].[CH3:24][O:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:25])[CH:15]=[C:14]2[C:12]1[N:11]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:31])([CH3:33])[CH3:32])[C:8]2=[N:9][CH:10]=[C:5]([CH2:4][NH2:1])[N:6]=[C:7]2[CH:13]=1

Participants

6

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 58010001HCID 58010001, compound

Product 2

HCID 14923Ammonium HydroxideYield 37%HCID 58009787HCID 58009787, compoundYield 116.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

2-(Azidomethyl)-6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (4.23 g, 9.12 mmol, Preparation #G.1) in THF (100 mL) was treated with triphenylphosphine (2.39 g, 9.12 mmol) and water (1.4 mL, 78 mmol). The mixture was heated at about 65° C. for about 4 h. The mixture was cooled to rt and concentrated under reduced pressure. The material was purified by flash chromatography on silica gel with 98:2 then 9:1 DCM/MeOH containing 2.5 vol % of a solution of 37% aqueous NH4OH to give (6-(5-methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine (2.32 g, 58%): LC/MS (Table 2, Method a) Rt=2.30 min; MS m/z 438 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. concentrationconcentrated under reduced pressure
  3. customThe material was purified by flash chromatography on silica gel with 98:2

Sources & evidence

ORD record
ord-17058c1c87e14dd3ad501150a728cd72
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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