Sodium Hydroxide → 1-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-4-carboxylic acid

HRID 1410031Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:30]=[CH:29][S:28][C:14]=3[N:15]=[C:16]([N:18]3[CH2:23][CH2:22][CH:21]([C:24]([O:26]C)=[O:25])[CH2:20][CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[Na+]>O1CCOCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:30]=[CH:29][S:28][C:14]=3[N:15]=[C:16]([N:18]3[CH2:23][CH2:22][CH:21]([C:24]([OH:26])=[O:25])[CH2:20][CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of methyl 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-4-carboxylate (150 mg, 0.35 mmol) in 7.5 mL of 1,4-dioxane and 7.5 mL of H2O was added NaOH (140 mg, 3.5 mmol) at room temperature. Then the reaction was stirred at 60° C. for 3 hours. The solvent was evaporated and the residue was suspended in 50 mL of H2O, then treated by 1N HCl until pH=5. The white solid was appeared and then filtered the solid was dried to give 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-4-carboxylic acid (130 mg, 90%) as a yellow solid

Workup

customThe solvent was evaporated
additiontreated by 1N HCl until pH=5
filtrationfiltered the solid
customwas dried

Sources & evidence

ORD record: ord-dac55bf809ff4d56a3266676e6718376
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921383B2

Reaction notes

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