Hydrochloric Acid → 2-(2-Amino-5-nitro-6-oxo-3,6-dihydropyrimidin-4-yl)-3-(thiophen-3-yl)propanenitrile

HRID 346110Notes

Reaction equation

[NH2:1][C:2]1[NH:3][C:4](=[O:25])[C:5]([N+:22]([O-:24])=[O:23])=[C:6]([C:8]([C:20]#[N:21])([CH2:14][C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)C(OCC)=O)[N:7]=1.Cl.[NH4+].[OH-]>[OH-].[Na+]>[NH2:1][C:2]1[NH:3][C:4](=[O:25])[C:5]([N+:22]([O-:24])=[O:23])=[C:6]([CH:8]([CH2:14][C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)[C:20]#[N:21])[N:7]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A solution of 2-Amino-α-cyano-1,6-dihydro-5-nitro-6-oxo-α-(3-thienyl-methyl)-4-pyrimidineacetic acid, ethyl ester in 1N NaOH (200 mL) is stirred for 2 h at room temperature and then acidified to pH 1 by the dropwise addition of conc HCl. The resulting suspension is warmed (45° C.) for 2 min and then cooled. The pH is adjusted to pH=3 with NH4OH. The solid is collected by filtration, washed with water, and dried under vacuum to give 2-Amino-1,6-dihydro-5-nitro-6-oxo-α-(3-thienylmethyl)-4-pyrimidineacetonitrile (3.03 g). ##STR19##

Workup

temperaturecooled
filtrationThe solid is collected by filtration
washwashed with water
customdried under vacuum

Sources & evidence

ORD record: ord-68ac4acfe0554c518e81f2d98cd181b1
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05061707

Reaction notes

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