Ammonium Hydroxide → (S)-4-Amino-6-((1-(1-methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylthio)pyrimidine-5-carbonitrile

HRID 75280Notes

Reaction equation

HRID 75280 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C@H:11]([C:13]2[N:18]=[C:17]3[CH:19]=[CH:20][N:21]([CH3:22])[C:16]3=[CH:15][C:14]=2[C:23]2[N:27]([CH3:28])[N:26]=[CH:25][CH:24]=2)[CH3:12])[N:5]=[C:4]([S:29][CH3:30])[N:3]=1.[OH-].[NH4+:32]>>[NH2:32][C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][C@H:11]([C:13]2[N:18]=[C:17]3[CH:19]=[CH:20][N:21]([CH3:22])[C:16]3=[CH:15][C:14]=2[C:23]2[N:27]([CH3:28])[N:26]=[CH:25][CH:24]=2)[CH3:12])[N:5]=[C:4]([S:29][CH3:30])[N:3]=1

Participants

3

Reactant 2

HCID 14923Ammonium Hydroxide2×HCID 86707967(S)-4-Chloro-6-((1-(1-methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylthio)pyrimidine-5-carbonitrile

Product 1

HCID 86707970(S)-4-Amino-6-((1-(1-methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylthio)pyrimidine-5-carbonitrile

Conditions

Temperature
85 °C

Procedure

A mixture of (S)-4-chloro-6-((1-(1-methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylthio)pyrimidine-5-carbonitrile (1.857 g, 4.23 mmol) and ammonium hydroxide (0.494 mL, 12.69 mmol) was heated at 85° C. in a microwave reactor for 12 hours. Additional ammonium hydroxide (0.494 mL, 12.69 mmol) was added. The reaction mixture was heated at 85° C. in a microwave reactor for 6 hours and then concentrated to give the title compound, which was used without further purification. ESI-MS m/z [M+H]+ calc'd for C20H21N9S, 420.16; found 420.4.

Workup

  1. temperatureThe reaction mixture was heated at 85° C. in a microwave reactor for 6 hours
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-89d669ab66dc49778c6fa5ece7f0c643
Source dataset
uspto-grants-2014_09
Patent number
US08835420B2

Reaction notes

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