Sodium Bicarbonate → HCID 15616694, compound

Reaction equation

[Br:1][C:2]1[N:6]2[C:7]([CH3:15])=[C:8]([CH2:13][CH3:14])[C:9]([O:11][CH3:12])=[N:10][C:5]2=[N:4][C:3]=1[C:16](=[O:27])[C:17]#[C:18][CH2:19][O:20]C1CCCCO1.C(=O)(O)[O-].[Na+]>CO.Cl>[Br:1][C:2]1[N:6]2[C:7]([CH3:15])=[C:8]([CH2:13][CH3:14])[C:9]([O:11][CH3:12])=[N:10][C:5]2=[N:4][C:3]=1[C:16](=[O:27])[C:17]#[C:18][CH2:19][OH:20]

Participants

Procedure

A solution of 5.0 g (11.5 mmol) of 1-(3-bromo-6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidin-2-yl)-4-(tetrahydropyran-2-yloxy)-2-butyn-1-one in a mixture of 100 ml of methanol and 35 ml of 2N hydrochloric acid stood at room temperature for 30 minutes and then was neutralized with aqueous sodium bicarbonate. Extraction with chloroform gave an oil which was chromatographed over silica (chloroform: ether: methanol 100:0:0 gradually changing to 0:95:5) to obtain 1.3 g (32%) of 1-(3-bromo-6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidin-2-yl)-4-hydroxy-2-butyn-1-one as off-white crystals melting at 212°-3° C. (decomp.).