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

HRID 1410095Notes

Reaction equation

HRID 1410095 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:29]=[CH:28][S:27][C:14]=3[N:15]=[C:16]([N:18]3[CH2:22][CH2:21][CH:20]([C:23]([O:25]C)=[O:24])[CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:29]=[CH:28][S:27][C:14]=3[N:15]=[C:16]([N:18]3[CH2:22][CH2:21][CH:20]([C:23]([OH:25])=[O:24])[CH2:19]3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68379089HCID 68379089, compound

Product 1

HCID 683794441-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidine-3-carboxylic acidYield 62.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of methyl 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidine-3-carboxylate (160 mg, 0.38 mmol) in 10 mL of methanol was added a solution of sodium hydroxide (154 mg, 3.8 mmol) in 2 mL of water at room temperature. Then the reaction mixture was stirred at this temperature for 24 hours. Then solvent was evaporated at 40° C. at reduced pressure and the residue was suspended in 30 mL of THF, then treated with 2N HCl to pH=2. The solvent was evaporated and the residue was dissolved in 50 mL of THF, then filtered and the filtrate was evaporated to give 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidine-3-carboxylic acid (95 mg, 61.4%) as a yellow solid. LC-MS: 402.1 [M+H]+, tR=1.33 min.

Workup

  1. customThen solvent was evaporated at 40° C. at reduced pressure
  2. additiontreated with 2N HCl to pH=2
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in 50 mL of THF
  5. filtrationfiltered
  6. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-de22eb227a534b85b03e2e11fd0fa5da
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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