Sodium Hydroxide → HCID 59514534, compound

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:32]=[CH:31][C:15]([CH2:16][C:17]2[N:22]=[C:21]([N:23]([CH3:25])[CH3:24])[C:20]([CH2:26][C:27]([O:29]C)=[O:28])=[CH:19][N:18]=2)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1.CO>[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][C:17]2[N:22]=[C:21]([N:23]([CH3:24])[CH3:25])[C:20]([CH2:26][C:27]([OH:29])=[O:28])=[CH:19][N:18]=2)=[CH:31][CH:32]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Procedure

To a mixture of methyl [2-(4-{[(benzyloxy)carbonyl]amino}benzyl)-4-(dimethylamino)pyrimidin-5-yl]acetate (1.51 g, 3.48 mmol) in tetrahydrofuran (8 mL) and methanol (15 mL) was added 1N NaOH aq. (5 mL). The reaction mixture was stirred for 20 hours at room temperature and concentrated under reduced pressure. The residue was neutralized with 1N hydrochloric acid and concentrated under reduced pressure. This residue was dissolved with chloroform/methanol (10:1) and the insolubles were removed by filtration. The filtrate was concentrated under reduced pressure. The residual solid was recrystallized with acetonitrile/ethanol (10:1) to give [2-(4-{[(benzyloxy)carbonyl]amino}benzyl)-4-(dimethylamino)pyrimidin-5-yl]acetic acid (1.14 g, 78%) as a white solid.