Hydrochloric Acid → (2-Aminopyrimidin-5-yl)boronic acid

HRID 341323Notes

Reaction equation

C(OC([NH:8][C:9]1[N:14]=[CH:13][C:12]([B:15]([OH:17])[OH:16])=[CH:11][N:10]=1)=O)(C)(C)C.Cl.[OH-].[Na+]>O>[NH2:8][C:9]1[N:14]=[CH:13][C:12]([B:15]([OH:17])[OH:16])=[CH:11][N:10]=1

Participants

Conditions

Temperature: 10 °C

Procedure

To a mixture of [2-[(tert-butoxycarbonyl)amino]pyrimidin-5-yl]boronic acid 12 (40.0 kg, 49 wt % by HPLC, 82.0 mol) in water (245 kg) was added concentrated hydrochloric acid (39.6 L) while maintaining the temperature below 30° C. The reaction mixture was stirred for 12 h and was then cooled to 10° C. The pH of the mixture was adjusted to 6.5 by addition of 50% aqueous sodium hydroxide solution while maintaining the temperature below 15° C. and the mixture was then stirred for 1 h. Water (69.0 kg) was added and the mixture was aged for 30 min. The resulting slurry was filtered and the cake was dried under vacuum at 50° C. to afford 2-aminopyrimidin-5-ylboronic acid III (10.2 kg, 90% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.50 (s, 2H), 7.97 (s, 2H), 6.74 (s, 2H).

Workup

temperaturewhile maintaining the temperature below 30° C
temperaturewhile maintaining the temperature below 15° C.
stirringthe mixture was then stirred for 1 h
waitthe mixture was aged for 30 min
filtrationThe resulting slurry was filtered
customthe cake was dried under vacuum at 50° C.

Sources & evidence

ORD record: ord-1e03f62a13cc48efa0d177beb8cdc87d
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895729B2

Reaction notes

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