Ammonium Chloride → 1-[5-(1H-Tetrazol-5-yl)pyrimidin-2-yl]piperidin-4-ol

HRID 729460Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][N:9]=2)[CH2:4][CH2:3]1.[N-:16]=[N+:17]=[N-:18].[Na+].[Cl-].[NH4+]>CN(C=O)C.[OH-].[Na+]>[NH:16]1[C:14]([C:11]2[CH:10]=[N:9][C:8]([N:5]3[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]3)=[N:13][CH:12]=2)=[N:15][N:18]=[N:17]1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 2-(4-hydroxypiperidin-1-yl)pyrimidine-5-carbonitrile (2 g, 9.79 mmol), sodium azide (0.955 g, 14.69 mmol) and ammonium chloride (1.048 g, 19.59 mmol) in DMF (24.48 mL) was heated at 130° C. for 1 h. The mixture was cooled to RT, diluted with 1N NaOH (5 mL), washed Et2O (2×10) mL. The aqueous layer was acidified to pH about 1 with 2 N HCl and placed in the refrigerator for 1 h. The solid was filtered and washed with water followed by Et2O. The solid was dried under high vacuum to afford the title compound.

Workup

temperatureThe mixture was cooled to RT
washwashed Et2O (2×10) mL
filtrationThe solid was filtered
washwashed with water
customThe solid was dried under high vacuum

Sources & evidence

ORD record: ord-d176f3303c2444acbd8ed0bf47698248
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582633B2

Reaction notes

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