Hydrogen Peroxide → 4-(Bicyclo[1.1.1]pentan-1-ylamino)-2-(methylthio)pyrimidine-5-carboxamide

HRID 2280834Notes

Reaction equation

[C:1]12([NH:6][C:7]3[C:12]([C:13]#[N:14])=[CH:11][N:10]=[C:9]([S:15][CH3:16])[N:8]=3)[CH2:5][CH:3]([CH2:4]1)[CH2:2]2.[OH:17]O.[OH-].[Na+]>CS(C)=O>[C:1]12([NH:6][C:7]3[C:12]([C:13]([NH2:14])=[O:17])=[CH:11][N:10]=[C:9]([S:15][CH3:16])[N:8]=3)[CH2:2][CH:3]([CH2:5]1)[CH2:4]2

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4-(bicyclo[1.1.1]pentan-1-ylamino)-2-(methylthio)-pyrimidine-5-carbonitrile (3.45 g, 14.9 mmol) in DMSO (15 mL) was added aqueous hydrogen peroxide solution (8.4 g, 30%, 74.5 mmol) and aqueous sodium hydroxide solution (12.4 mL, 6 mol/L, 74.5 mmol) at 0° C. The mixture was stirred at 50° C. for 15 min and then quenched by the addition of water (30 mL). The solid formed was collected and dried under vacuum to give the desired product (3.5 g, 14.0 mmol, 94% yield). MS (ESI)/m/z=251.2 [M+1]+.

Workup

customquenched by the addition of water (30 mL)
customThe solid formed
customwas collected
customdried under vacuum

Sources & evidence

ORD record: ord-37a36fa2b22a4ac9ad0ecc8d9e4a9214
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139534B2

Reaction notes

Loading…