Trityl chloride → 5-Amino-1-[2-(trityloxy)ethyl]pyrazole-4-carbonitrile

HRID 349532Notes

Reaction equation

[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][OH:9])[N:5]=[CH:4][C:3]=1[C:10]#[N:11].[C:12]1([C:18](Cl)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][O:9][C:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:5]=[CH:4][C:3]=1[C:10]#[N:11]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 5-amino-1-(2-hydroxyethyl)pyrazole-4-carbonitrile (10 g, 65.7 mmol) and pyridine (100 ml) was added triphenylmethyl chloride (22.3 g, 78.9 mmol) at room temperature. After stirring at 60° C. for 6 hours, the reaction mixture was concentrated in vacuo. To the residue were added tetrahydrofuran and brine, and the separated organic layer was washed with brine. The extract was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with ethyl acetate to give 5-amino-1-[2-(trityloxy)ethyl]pyrazole-4-carbonitrile (25.4 g) as a colorless solid.

Workup

concentrationthe reaction mixture was concentrated in vacuo
additionTo the residue were added tetrahydrofuran and brine
washthe separated organic layer was washed with brine
dry with materialThe extract was dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record: ord-968dc57983c84bc1a06f349e3c975ef6
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179801B2

Reaction notes

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