Sodium Hydroxide → 6-Amino-3-cyclopropyl-1-(2-fluoro-4-iodophenyl)pyrimidine-2,4(1H,3H)-dione

HRID 75657Notes

Reaction equation

[C:1]([CH2:3][C:4]([N:6]([CH:18]1[CH2:20][CH2:19]1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=1[F:17])=[O:8])=[O:5])#[N:2].[OH-].[Na+]>O>[NH2:2][C:1]1[N:9]([C:10]2[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=2[F:17])[C:7](=[O:8])[N:6]([CH:18]2[CH2:19][CH2:20]2)[C:4](=[O:5])[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To 1-(2-cyano-acetyl)-1-cyclopropyl-3-(2-fluoro-4-iodo-phenyl)-urea 74 (192 g) were added water (962 ml) and 2N aqueous sodium hydroxide solution (24.9 ml), and the mixture was stirred with heating at 80° C. for 1 hr. After allowing to cool to room temperature, the crystals were collected by filtration and dried to give 6-amino-3-cyclopropyl-1-(2-fluoro-4-iodo-phenyl)-1H-pyrimidine-2,4-dione 75 (178 g, yield from 48, 88%) as pale-yellow crystals.

Workup

temperatureto cool to room temperature
filtrationthe crystals were collected by filtration
customdried

Sources & evidence

ORD record: ord-4e550ef727b040ed828be342f0059812
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835443B2

Reaction notes

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