Ammonium Hydroxide → HCID 131731114, compound

HRID 1916122Notes

Reaction equation

CS([C:5]1[N:10]=[C:9]([NH:11][C@H:12]2[CH2:17][CH2:16][CH2:15][N:14]([S:18]([CH2:21][CH:22]([CH3:24])[CH3:23])(=[O:20])=[O:19])[CH2:13]2)[C:8]([C:25]2[N:26]=[C:27]3[CH:33]=[CH:32][N:31]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[C:28]3=[N:29][CH:30]=2)=[CH:7][N:6]=1)(=O)=O.[OH-].[NH4+:43]>O1CCOCC1>[CH3:24][CH:22]([CH3:23])[CH2:21][S:18]([N:14]1[CH2:15][CH2:16][CH2:17][C@H:12]([NH:11][C:9]2[C:8]([C:25]3[N:26]=[C:27]4[CH:33]=[CH:32][N:31]([CH2:34][O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])[C:28]4=[N:29][CH:30]=3)=[CH:7][N:6]=[C:5]([NH2:43])[N:10]=2)[CH2:13]1)(=[O:20])=[O:19]

Participants

Conditions

Temperature: 90 °C

Procedure

In a 10 mL sealed tube {2-methanesulfonyl-5-[5-(2-trimethysilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-yl}-[(S)-1-(2-methyl-propane-1-sulfonyl)-piperidin-3-yl]-amine (38 mg, 609 μmol) and ammonium hydroxide (450 mg, 0.5 ml, 12.8 mmol) were combined with 1,4-dioxane (2 ml) to give a light yellow solution. The reaction mixture was heated to 90° C. and stirred for 6 h. It was concentrated and diluted with water, extracted with ethyl acetate (2×20 ml). The organic layers were dried (MgSO4) and concentrated to give N*4*-[(S)-1-(2-methyl-propane-1-sulfonyl)-piperidin-3-yl]-5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidine-2,4-diamine as a yellow foaming solid. MS (ES+): 561.

Workup

customto give a light yellow solution
concentrationIt was concentrated
additiondiluted with water
extractionextracted with ethyl acetate (2×20 ml)
dry with materialThe organic layers were dried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-9300cd6124cc4fb988d82ea1c00a8542
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618103B2

Reaction notes

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