Hydrochloric Acid → 2-(4-(tert-butoxycarbonyl)piperazin-1-yl)pyrimidine-5-carboxylic acid

HRID 522649Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[CH:18][C:17]([C:20]([O:22]CC)=[O:21])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>C1COCC1.CO.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[N:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl 2-(4-(tert-butoxycarbonyl)piperazin-1-yl)pyrimidine-5-carboxylate (17 g, crude) in THF/methanol/H2O (300 mL) was added sodium hydroxide (4.3 g, 107.5 mmol), and the reaction mixture was stirred at 70 0° C. for 2 hours. LCMS showed the reaction was completed. The reaction mixture was brought to pH≈5-6 with 1 M HCl, and then filtered. The solid was collected and dried to give 2-(4-(tert-butoxycarbonyl)piperazin-1-yl)pyrimidine-5-carboxylic acid as a white solid (16 g, 96%), which was directly used in the next step without further purification. MS (ES+) C14H20N4O4 requires: 308, found: 253 [M-56+H]+.

Workup

filtrationfiltered
customThe solid was collected
customdried

Sources & evidence

ORD record: ord-ce662020662b47349a923fd94b2b6212
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334263B2

Reaction notes

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