Water → N-(2-(Benzylthio)-6-{[2-hydroxy-1-(hydroxymethyl)ethyl]amino}-pyrimidin-4-yl)methanesulfonamide

HRID 424658Notes

Reaction equation

[CH2:1]([S:8][C:9]1[N:14]=[C:13]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[C:11]([NH:20][CH2:21][CH2:22][OH:23])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NC(CO)[CH2:26][OH:27].CCOC(C)=O.O>CN1C(=O)CCC1>[CH2:1]([S:8][C:9]1[N:14]=[C:13]([NH:15][S:16]([CH3:19])(=[O:17])=[O:18])[CH:12]=[C:11]([NH:20][CH:21]([CH2:26][OH:27])[CH2:22][OH:23])[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of the subtitle product of Example 19 step (0.20 g) in NMP (0.5 ml) was added 2-aminopropane-1,3-diol (1.0 g) and the reaction was heated at 100° C. for 2 days. To the reaction was added EtOAc (50 ml) and H2O (50 ml). The organic layer was separated and washed with H2O (2×20 ml) and brine (20 ml). The organic layer was dried (MgSO4) and the solvent removed under reduced pressure to give a solid. This was purified by column chromatography (1:1 EtOAc/iso-hexane then EtOAc) to give the title compound as a solid.

Workup

customThe organic layer was separated
washwashed with H2O (2×20 ml) and brine (20 ml)
dry with materialThe organic layer was dried (MgSO4)
customthe solvent removed under reduced pressure
customto give a solid
customThis was purified by column chromatography (1:1 EtOAc/iso-hexane

Sources & evidence

ORD record: ord-3d463039994d4b47855cc94ff8534a7f
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106063B2

Reaction notes

Loading…